Positive allosteric modulators of sweet taste

ABSTRACT

The invention provides natural allosteric modulators that are useful as sweet flavor enhancers. The present invention also includes ingestible compositions comprising the present compounds and methods of enhancing the sweet taste of sweeteners and sugars.

CROSS-REFERENCE TO A RELATED APPLICATION

This application claims the priority benefit of U.S. Provisional Application Ser. No. 62/423,001, filed Nov. 16, 2016, which is incorporated herein by reference in its entirety.

BACKGROUND OF INVENTION

Living things use sensory systems to detect important information about the environment in which they live. Taste is a particularly important sensory system, and is one of the most sophisticated forms of chemically-triggered sensations found throughout the animal kingdom.

Mammals are believed to have five basic taste modalities: sweet, bitter, sour, salty, and umami (savory). The pleasant taste associated with sweetness is important in industries that produce consumable materials. Natural sugars, such as sucrose, fructose, and glucose, for example, are heavily utilized by the beverage, food, pharmaceutical, and oral hygienic/cosmetic industries. However, many consumers are required to control or reduce the sugar and calorie content of their diets due to health concerns such as obesity, diabetes, and heart disease. Thus, there is a continuing need in the market to provide alternative, non-caloric or low-caloric sweeteners with sugar-like taste for consumers who need or desire to limit caloric intake.

One option for addressing this need is the use of natural high-potency sweeteners (NHPS). Because these sweeteners are many times sweeter than sucrose, for example, much less of the sweetener is required to replace the sugar; however, these sweeteners often possess taste qualities that vary from those of natural sugars. For example, certain sweetening compositions have different temporal profiles, maximal responses, flavor profiles, mouthfeel, and/or adaptation behaviors from those of sugar. In addition, high-potency sweeteners generally exhibit bitter, metallic, cooling, astringent, or licorice-like aftertastes, and/or diminishing sweetness on iterative tasting. These properties can be undesirable for consumers.

Therefore, improved compounds and methods for enhancing the sweetness of consumable materials, while retaining the characteristics of sugar and keeping calorie content low, are desired.

It is known that sensations associated with taste involve distinct signalling pathways mediated by receptors, which specifically recognize molecules that elicit those taste sensations. Recent developments in sweetening methods include the use of certain molecules that enhance the sweet taste of existing sweeteners and sugars, rather than acting as sweeteners themselves. The following disclosure provides new, natural positive modulator compounds for enhancing sweet taste.

BRIEF SUMMARY

The present invention provides isolated compounds for enhancing sweet taste, ingestible compositions containing these compounds, and methods of preparing such ingestible compositions, to help meet the need for improved consumer-friendly, low-calorie sweetened products.

The present invention further provides improved methods of enhancing, modulating, or potentiating the perception, by a subject, of the sweet taste of an ingestible composition, such as a food, beverage, or pharmaceutical product.

Further provided are improved methods for modulating, particularly enhancing or potentiating, the activation of a sweet taste receptor.

Embodiments of the invention provide improved natural sweet taste modulators that enhance sweet taste receptor activity and sweetness perception while reducing the required concentration of, for example, an artificial sweetener or sugar. In certain embodiments, the sweet taste modulator is any one of the compounds from Table 1, or a combination thereof, or a salt or derivative thereof.

The sweet taste modulator can be combined with any suitable sweetener, such as, for example, a natural caloric sweetener; a natural high-potency sweetener; a synthetic sweetener, including synthetic high-potency sweeteners; sugar alcohols; rare sugars; sweetener enhancers; or combinations thereof, to provide an ingestible composition having enhanced sweetness.

In another embodiment, the present invention provides a method of increasing the sweet taste of an ingestible composition by adding a compound of the present invention to the ingestible composition. The compound used according to the current invention can be a chemosensory receptor modifier, a chemosensory receptor ligand modifier, or both, e.g., a partial chemosensory receptor modifier and partial chemosensory receptor ligand modifier. For example, the compound of the present invention can be a sweet receptor agonist, or a sweet enhancer, or a partial sweet receptor agonist and partial sweet enhancer.

In another embodiment, the present invention provides an ingestible composition comprising the sweet taste modulator and an ingestibly-acceptable excipient. According to particular embodiments, the ingestible composition can be a product selected from beverages, foods, pharmaceuticals, tobacco products, oral hygienic/cosmetics, nutraceuticals, and the like.

In yet another embodiment, the present invention provides a flavoring concentrate formulation comprising a compound of the present invention as a flavor modifying ingredient, a carrier, and optionally, at least one adjuvant.

DETAILED DISCLOSURE

The present invention provides isolated compounds for enhancing sweet taste, ingestible compositions containing such compounds, and methods of preparing such ingestible compositions to help meet the need for improved low-calorie sweetened products.

The present invention further provides improved methods of enhancing, modulating, and/or potentiating the sweet taste of an ingestible composition, such as a food, beverage, or pharmaceutical product. The present invention also provides an improved method of modulating, particularly enhancing or potentiating, the activation of a sweet taste receptor.

The compounds of the invention include all stereochemical forms of the compound, including geometric isomers (i.e., E, Z) and optical isomers (i.e., R, S). Single stereochemical isomers as well as enantiomeric and diastereomeric mixtures of the present compounds are specifically contemplated. The compounds may also exist in several tautomeric forms. The term “tautomer” as used herein refers to isomers that change into one another with great ease such that they can exist together in equilibrium. Accordingly, the chemical structures depicted herein encompass all possible tautomeric forms of the illustrated compounds. Additionally, unless otherwise stated, formulas depicted herein are also meant to include compounds that differ only in the presence of one or more isotopically enriched atoms.

Further included within the scope of the present invention are various forms and derivatives of the exemplified compounds. Such forms include, but are not limited to, unsolvated, solvated, and hydrated forms. Further, derivative forms include, but are not limited to, acylated derivatives, alkylated derivatives, amidated derivatives, esterified derivatives, and other like derivatives. Furthermore, the compounds may exist in multiple crystalline or amorphous forms. In general, all physical forms are contemplated herein and are within the scope of the present invention.

Selected Definitions

As used herein, an “ingestible composition” includes any substance that, either alone or together with another substance, can be ingested orally, whether intended for consumption or not. Ingestible compositions include, for example, “food or beverage products,” “pharmaceuticals,” as well as “non-edible products.” By “food or beverage products,” it is meant any edible product intended for consumption by humans or animals, including solids, semi-solids, and liquids (e.g., beverages). The term “non-edible products” or “non-comestible composition” includes any product or composition that can be taken orally by humans or animals for purposes other than consumption as food or beverage. For example, non-edible products and noncomestible compositions include pharmaceuticals and over the counter medications, oral care products such as dentifrices and mouthwashes, cosmetic products such as sweetened lip balms and other personal care products.

An “ingestibly acceptable carrier or excipient” is a medium and/or composition that is used to prepare a desired form of an inventive compound of the subject invention, in order to administer the compound. The medium and/or composition may be in any form depending on the intended use of a product, e.g., solid, semi-solid, liquid, paste, gel, cream, foamy material, suspension, solution, or any combination thereof (such as a liquid containing solids). Ingestibly acceptable carriers include many common food ingredients, such as water at neutral, acidic, or basic pH; fruit or vegetable juices; vinegar; marinades; beer, wine; natural water/fat emulsions such as milk or condensed milk; edible oils and shortenings; fatty acids and their alkyl esters; low molecular weight oligomers of propylene glycol; glyceryl esters of fatty acids; and dispersions or emulsions of such hydrophobic substances in aqueous media; salts such as sodium, calcium or potassium chloride; wheat flours; solvents such as ethanol; solid edible diluents such as vegetable powders or flours; other liquid vehicles; dispersion or suspension aids; surface active agents; isotonic agents; thickening or emulsifying agents; preservatives; solid binders; lubricants and the like.

According to the present invention, a “chemosensory receptor” can be any receptor associated with chemosensory sensation or chemosensory ligand triggered signal transduction, e.g., via taste receptors or taste-related receptors expressed in taste buds or internal organs of the body, such as in the gastrointestinal tract, etc. In one embodiment, a chemosensory receptor is a receptor that belongs to the 7-transmembrane receptor superfamily or G protein-coupled receptors (GPCRs). In another embodiment, a chemosensory receptor is a receptor carrying out signal transduction via one or more G proteins. In yet another embodiment, a chemosensory receptor is a receptor that belongs to family C or class C of GPCRs. In yet another embodiment, a chemosensory receptor is a receptor that belongs to the TIR family. In yet another embodiment, a chemosensory receptor is a receptor of TIR1, TIR2, TIR3, or their equivalents or variants or a combination thereof. In still another embodiment, a chemosensory receptor is a hetero-dimer of TAS1R2 and TAS1R3, or their equivalent or variant.

An “enhancer” refers to a compound that modulates (increases) the activation of a particular receptor, preferably a chemosensory, e.g., the TAS1R2/TAS1R3 receptor. Such enhancers typically enhance the activation of a chemosensory receptor by its ligand. Typically the “enhancer” will be specific to a particular ligand, i.e., it will not enhance the activation of a chemosensory receptor by chemosensory ligands other than the particular chemosensory ligand, or ligands closely related thereto.

Some enhancers, at their ligand-enhancing concentration, do not result in activation of the particular receptor by themselves. That is, the ligand-enhancing concentrations of these enhancers are concentration levels of the enhancers that increase or enhance the activation of a particular receptor by a ligand without substantially activating the particular receptor by the enhancers themselves. In some embodiments, certain enhancers, when used at a concentration higher than the ligand-enhancing concentration, can also activate a particular receptor by themselves in addition to modulating the activation of the receptor. For example, certain enhancers, when used at a concentration higher than the ligand-enhancing concentration, can be sweeteners (i.e., sweet flavoring agent/entity) as well. In other embodiments, certain enhancers can activate a particular receptor by themselves in addition to modulating the activation of the receptor simultaneously at the same concentration. In other words, certain enhancers are also sweeteners (i.e., sweet flavoring agent/entity) at the same time.

A “flavor” refers to the perception of taste in a subject, which includes sweet, sour, salty, bitter and umami. The subject may be a human or an animal.

A “flavoring agent” refers to a compound that induces a flavor or taste in an animal or a human. The flavoring agent can be natural, semi-synthetic, or synthetic.

A “flavor modifier” or “flavor modifying agent” refers to a compound that modulates, including enhancing or potentiating, and/or inducing, the tastes of a flavoring agent in an animal or a human.

A “flavor enhancer” refers to a compound that enhances the taste of a flavoring agent, or an ingestible composition comprising the flavoring agent.

A “sweet flavor” refers to the sweet taste typically induced by sugar, such as sucrose or fructose, in an animal or a human.

A “sweet flavoring agent,” “sweet flavor entity,” “sweetener,” or “sweet compound” refers to a compound that elicits a detectable sweet flavor in a subject, e.g., fructose or a compound that activates a TAS1R2/TAS1R3 receptor. The subject may be a human or an animal.

A “sweet flavor modifier” or “sweet flavor modifying agent” refers to a compound that modulates, including enhancing or potentiating, inducing, or blocking, the sweet taste of a sweet flavoring agent in an animal or a human. The sweet flavor modifier includes both sweet flavor enhancer and sweet flavoring agent.

A “sweet flavor enhancer” or “sweet flavor enhancing agent” refers to an enhancer of a sweet flavor.

A “sweet receptor activating compound” or “sweet receptor agonist” refers to a compound that activates a sweet receptor, such as, for example, a TAS1R2/TAS1R3 receptor. One example of a sweet receptor activating compound is a sweetener, such as sucrose or fructose.

A “sweet receptor modulating compound” refers to a compound that modulates (activates, blocks, or enhances/reduces activation of) a sweet receptor such as a TAS1R2/TAS1R3 receptor.

A “sweet receptor enhancing compound” refers to a compound that enhances or potentiates the effect of a sweet receptor activating compound.

A “sweet flavor modulating amount” refers to an amount of a compound that is sufficient to alter (either increase or decrease) sweet taste in an ingestible composition sufficiently to be perceived by a human subject. In many embodiments of the invention, at least about 0.001 ppm of the compound would need to be present in order for most human subjects to perceive a modulation of the sweet flavor of an ingestible composition comprising the compound. A broad range of concentrations that can be employed in order to provide a desirable degree of sweet flavor modulation can be from about 0.001 ppm to 100 ppm, or a narrow range from about 0.1 ppm to about 10 ppm. Alternative ranges of sweet flavor modulating amounts can be from about 0.01 ppm to about 30 ppm, from about 0.05 ppm to about 15 ppm, from about 0.1 ppm to about 5 ppm, or from about 0.1 ppm to about 3 ppm.

A “sweet flavor enhancing amount” refers to an amount of a compound that is sufficient to enhance the taste of flavoring agents, e.g., sucrose or fructose, in an ingestible composition, as perceived by an animal or a human. A broad range of a sweet flavor enhancing amount can be from about 0.001 ppm to 100 ppm, or a narrow range from about 0.1 ppm to about 10 ppm. Alternative ranges of sweet flavor enhancing amounts can be from about 0.01 ppm to about 30 ppm, from about 0.05 ppm to about 15 ppm, from about 0.1 ppm to about 5 ppm, or from about 0.1 ppm to about 3 ppm. In some embodiments, sweet flavor enhancing amount is the amount corresponding to ligand enhancing concentration(s) of a sweet flavor enhancer of the present invention.

A “sweet receptor modulating amount” refers to an amount of a compound that is sufficient to modulate (activate, enhance or block) a sweet taste receptor protein. In many embodiments of the invention, a sweet receptor modulating amount is at least about 10 nM, or at least about 100 nM, or at least about 1 μM, or at least about 10 μM.

A “TAS1R2/TAS1R3 receptor modulating or activating amount” is an amount of compound that is sufficient to modulate or activate a TAS1R2/TAS1R3 receptor.

A “sweet receptor” is a taste receptor that can be modulated by a sweet compound. Preferably a sweet receptor is a G protein coupled receptor, and more preferably the sweet receptor is a TAS1R2/TAS1R3 receptor.

The terms “isolated,” and “purified,” refer to material that is substantially or essentially free from components that normally accompany the compound as found in its native state. Purity and homogeneity are typically determined using analytical chemistry techniques. Particularly, in preferred embodiments, the compound is at least 85% pure, more preferably at least 90% pure, more preferably at least 95% pure, and most preferably at least 99% pure.

Compounds of the Current Invention

In specific embodiments, the present invention provides sweet taste modulator compounds as shown in Table 1, as well as derivatives of the compounds exemplified in Table 1. In preferred embodiments, these compounds are isolated or purified.

The materials used in preparing the compounds of the invention, e.g., the various structural subclasses and species of the compounds or the synthetic precursors of the present compounds, are known compounds, or can be synthesized by known methods described in the literature, or are commercially available from various sources well known to those of ordinary skill in the art. These sources can be, for example, Sigma-Aldrich Corporation of St. Louis, Mo. USA and their subsidiaries Fluka and Riedel-de Haen, at their various other worldwide offices, and other well-known chemical suppliers such as Fisher Scientific, TCI America of Philadelphia, Pa., ChemDiv of San Diego, Calif., Chembridge of San Diego, Calif., Asinex of Moscow, Russia, SPECS/BIOSPECS of the Netherlands, Maybridge of Cornwall, England, Acros, TimTec of Russia, Comgenex of South San Francisco, Calif., and ASDI Biosciences of Newark, Del.

The skilled artisan in the art of organic chemistry can readily carry out the synthesis of many starting materials and subsequent manipulations without further direction. These include, for example, reduction of carbonyl compounds to their corresponding alcohols; oxidations; acylations; aromatic substitutions; both electrophilic and nucleophilic; etherifications; esterification; saponification; nitrations; hydrogenations; reductive animation and the like. These manipulations are discussed in standard texts such as March's Advanced Organic Chemistry (3d Edition, 1985, Wiley-Interscience, New York), Feiser and Feiser's Reagents for Organic Synthesis, and in the various volumes and editions or Methoden der Organischen Chemie (Houben-Weyl), and the like. Many general methods for preparation of materials comprising variously substituted heterocyclic, hetereoaryl, and aryl rings (the precursors of Ar, hAr1, and/or hAr2) can be found in Methoden der Organischen Chemie (Houben-Weyl), whose various volumes and editions are available from Georg Thieme Verlag, Stuttgart. The entire disclosures of the treatises recited above are hereby incorporated by reference in their entireties for their teachings regarding methods for synthesizing organic compounds and their precursors.

The skilled artisan will also readily appreciate that certain reactions are best carried out when other functionality is masked or protected in the molecule, thus avoiding any undesirable side reactions and/or increasing the yield of the reaction. Often the skilled artisan utilizes protecting groups to accomplish such increased yields or to avoid the undesired reactions. These reactions are found in the literature and are also well within the scope of the skilled artisan. Examples of many of these manipulations can be found for example in T. Greene and P. Wuts, Protecting Groups in Organic Synthesis, 3r Ed., John Wiley & Sons (1999).

Use of the Compounds of the Subject Invention to Enhance Sweeteners

The compounds of Table 1, and derivatives thereof, can be used for one or more methods of the present invention. In one embodiment, the method can include increasing or enhancing sweet flavor. In another embodiment, the method can include modulating a sweet receptor and/or its ligand.

According to the present invention, a method of modulating a chemosensory receptor and/or its ligand can include modulating the activity, structure, function, expression, and/or modification of a chemosensory receptor as well as modulating, treating, or taking prophylactic measure of a condition, e.g., physiological or pathological condition, associated with a chemosensory receptor.

In general, the compounds of the present invention, individually or in combination, can be provided in a composition, such as, for example, an ingestible composition. In one embodiment, the compounds of the subject invention impart a more sugar-like temporal profile and/or flavor profile to a sweetener composition by combining one or more of the compounds with one or more sweeteners in a sweetener composition. In another embodiment, the compounds increase or enhance the sweet taste of a composition. In another embodiment, the compounds can be in a composition that modulates the sweet receptors and/or their ligands expressed at a place in the body other than in the taste buds.

The compounds or combination of compounds selected from Table 1 should preferably be comestibly acceptable, e.g., deemed suitable for consumption in food or drink, from the perspective of giving the comestible compositions an improved and/or pleasing sweet taste, and are not toxic and do not cause unpleasant or undesirable pharmacological or toxicological effects on a human or other animal at the typical concentrations they are employed as flavoring agents for the comestible compositions.

One of the methods of demonstrating that a flavorant compound is comestibly acceptable is to have the compound tested and/or evaluated by an Expert Panel of the Flavor and Extract Manufacturers Association (FEMA) and declared as to be “Generally Recognized As Safe” (“GRAS”). The FEMA/GRAS evaluation process for flavorant compounds is complex but well known to those of ordinary skill in the food product preparation arts, as is discussed by Smith, et al. in an article entitled “GRAS Flavoring Substances 21,” Food Technology, 57(5), pgs 46-59, May 2003, the entire contents of which are hereby incorporated herein by reference.

In addition to the FEMA expert panel, an independent, qualified panel of experts in pertinent scientific disciplines may be formed by the manufacturer to evaluate the safety of a specific compound for GRAS status. This process is known as a “self-determination of GRAS status.”

Another method of demonstrating that a flavorant compound is comestibly acceptable is to obtain favorable review by the WHO/FAO Joint Expert Committee on Food Additives, or JECFA. There are also other evaluation methods, such as independent review by the regulatory agency, which are generally known to those of ordinary skill in the food product preparation arts.

In one embodiment, the compounds of the present invention can be used at concentrations within acceptable oral toxicity levels. In another embodiment, the compounds of the present invention can be used at ligand enhancing concentrations, e.g., very low concentrations on the order of a few parts per million, in combination with one or more known sweeteners, natural or artificial, so as to reduce the concentration of the known sweetener required to prepare an ingestible composition having the desired degree of sweetness.

The compounds can be used to enhance the sweet taste or perception of sweet taste of any suitable caloric, low-caloric, or non-caloric sweetener. Non-limiting examples of such sweeteners include caloric carbohydrate sweeteners (including polyols), natural high-potency sweeteners, synthetic high-potency sweeteners, and combinations thereof.

As used herein, the phrase “natural high-potency sweetener” or “NHPS” means any sweetener found in nature, which may be in raw, extracted, purified, or any other form, singularly or in combination thereof and characteristically having a sweetness potency greater than sucrose, fructose, or glucose, but having fewer calories. Non-limiting examples of NHPSs include rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside A, dulcoside B, rubusoside, stevia, stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener, siamenoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, and cyclocarioside I.

As used herein, the phrase “synthetic sweetener” or “synthetic high-potency sweetener” refers to any composition that is not found in nature and that has a sweetness potency greater than sucrose, fructose, or glucose, yet has fewer calories. Non-limiting examples of synthetic sweeteners include sucralose, acesulfame potassium or other salts, aspartame, alitame, saccharin, neohesperidin dihydrochalcone, cyclamate, neotame, N-[3-(3-hydroxy-4-methoxyphenyl)propyl]-L-α-aspartyl]-L-phenylalanine 1-methyl ester, N-[3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl]-L-α-aspartyl]-L-phenylalanine 1-methyl ester, N-[3-(3-methoxy-4-hydroxyphenyl)propyl]-L-α-aspartyl]-L-phenylalanine 1-methyl ester, salts thereof, and the like.

According to the present invention, NHPS and synthetic sweeteners can be used individually or in combination with other NHPSs and/or synthetic sweeteners. For example, the sweetener composition can comprise a single NHPS or a single synthetic sweetener; a single NHPS in combination with a single synthetic sweetener; one or more NHPSs in combination with a single synthetic sweeteners; a single NHPS in combination with one or more synthetic sweeteners; or one or more NHPSs in combination with one or more synthetic sweeteners. A plurality of NHPSs and/or synthetic sweeteners can be used so long as the combined effect does not adversely affect the taste of the sweetener composition or orally sweetened composition.

In one embodiment, the present compounds can enhance the sweetness of a sweetener under a broad range of pH, e.g., from acid pH to basic pH. The pH can be, for example, from about 2.5 to about 9.0; from about 2.5 to about 8.0; from about 2.8 to about 7.5; from about 3.0 to about 7, and from about 3.5 to about 7.

In certain embodiments, the present compounds can enhance the perceived sweetness of a fixed concentration of a sweetener in taste tests at a compound concentration of about 50 μM, 40 μM, 30 μM, 20 μM, or 10 μM at acidic to basic pH. In certain embodiments, the enhancement factor of the present compounds at the lower pH is substantially similar to the enhancement factor of the compounds at neutral pH.

Furthermore, in some embodiments, the present compounds have enhanced photostability. That is, when exposed to a light source, the compounds have stability and are less prone to degradation. Such photostability and consistent sweet enhancing property under a broad range of pH's render the compounds good candidates for use in a wide variety of foods and beverages.

Typically, at least a sweet receptor modulating amount, a sweet receptor ligand modulating amount, a sweet flavor modulating amount, a sweet flavoring agent amount, a sweet flavor enhancing amount, or a therapeutically effective amount of one or more of the present compounds will be added to the ingestible composition, optionally in the presence of known sweeteners, e.g., so that the sweet flavor modified ingestible composition has an increased sweet taste as compared to the ingestible composition prepared without the compounds of the present invention, as judged by human beings or animals in general, or in the case of formulations testing, as judged by a majority of a panel of at least eight human taste testers, via procedures commonly known in the field.

The concentration of sweet flavoring agent needed to modulate or improve the flavor of the ingestible composition will of course depend on many variables, including the specific type of the ingestible composition and its various other ingredients, especially the presence of other known sweet flavoring agents and the concentrations thereof, the natural genetic variability and individual preferences and health conditions of various human beings tasting the compositions, and the subjective effect of the particular compound on the taste of such chemosensory compounds.

One application of the present compounds is for modulating (inducing, enhancing or inhibiting) the sweet taste or other taste properties of natural or synthetic sweeteners, and ingestible compositions made therefrom. In one embodiment, the compounds of the present invention are used or provided in their ligand enhancing concentration(s).

In one embodiment, the present invention provides a sweet enhancing composition. The sweet enhancing composition comprises a compound of the present invention in an amount effective to enhance sweetening, e.g., sweet flavor enhancing amount in combination with a first amount of sweetener, wherein the sweetening is more than the sweetening provided by the first amount of sweetener without the compound of the subject invention.

In one embodiment, the present invention provides an ingestible composition that comprises the sweet enhancing composition of the present invention. In certain embodiments, the ingestible composition is in the form of a food or beverage product, a pharmaceutical composition, a nutritional product, a dietary supplement, over-the-counter medication, or oral care product.

Noncomestible Products

In certain embodiments, a compound of the present invention is added to a noncomestible composition or non-edible product, such as a pharmaceutical product, over the counter (OTC) product, oral care product, cosmetic product such as sweetened lip balms, or other personal care product.

Over the counter (OTC) product and oral care product refer to products for household and/or personal use that may be sold without a prescription and/or without a visit to a medical professional. Examples of OTC products include, but are not limited to, vitamins and dietary supplements; topical analgesics and/or anesthetics; cough, cold and allergy remedies; antihistamines and/or allergy remedies; and combinations thereof.

Vitamins and dietary supplements include, but are not limited to, vitamins, dietary supplements, tonics/bottled nutritive drinks, child-specific vitamins, dietary supplements, and any other such products.

Topical analgesics and/or anesthetics include any topical creams/ointments/gels used to alleviate superficial or deep-seated aches and pains, e.g., muscle pain; teething gel; patches with analgesic ingredient; and combinations thereof.

Cough, cold and allergy remedies include, but are not limited to, decongestants; cough remedies; pharyngeal preparations; medicated confectioneries; antihistamines and child-specific cough, cold and allergy remedies; and combination products.

Antihistamines and/or allergy remedies include, but are not limited to, any systemic treatments for hay fever, nasal allergies, and insect bites and stings.

Examples of oral care products include, but are not limited to mouth cleaning strips, toothpaste, toothbrushes, mouthwashes/dental rinses, denture care, mouth fresheners at-home teeth whiteners, dentifrices, and dental floss.

Food and Beverage Products

In another embodiment, the present compounds are added to food or beverage products or formulations. Examples of food and beverage products or formulations include, but are not limited to sweet coatings, frostings, or glazes for comestible products or any entity included in the Soup category, the Dried Processed Food category, the Beverage category, the Ready Meal category, the Canned or Preserved Food category, the Frozen Processed Food category, the Chilled Processed Food category, the Snack Food category, the Baked Goods category, the Confectionary category, the Dairy Product category, the Ice Cream category, the Meal Replacement category, the Pasta and Noodle category, and the Sauces, Dressings, Condiments category, the Baby Food category, and/or the Spreads category.

In general, the Soup category refers to canned/preserved, dehydrated, instant, chilled, UHT and frozen soup. For the purpose of this definition soup(s) means a food prepared from meat, poultry, fish, vegetables, grains, fruit and other ingredients, cooked in a liquid that may include visible pieces of some or all of these ingredients. It may be clear (as a broth) or thick (as a chowder), smooth, pureed or chunky, ready-to-serve, semi-condensed or condensed and may be served hot or cold, as a first course or as the main course of a meal or as a between meal snack (sipped like a beverage). Soup may be used as an ingredient for preparing other meal components and may range from broths (consomme) to sauces (cream or cheese-based soups).

The Dehydrated and Culinary Food Category means: (i) Cooking aid products such as: powders, granules, pastes, concentrated liquid products, including concentrated bouillon, bouillon and bouillon like products in pressed cubes, tablets or powder or granulated form, which are sold separately as a finished product or as an ingredient within a product, sauces and recipe mixes (regardless of technology); (ii) Meal solutions products such as: dehydrated and freeze dried soups, including dehydrated soup mixes, dehydrated instant soups, dehydrated ready-to-cook soups, dehydrated or ambient preparations of ready-made dishes, meals and single serve entrees including pasta, potato and rice dishes; and (iii) Meal embellishment products such as: condiments, marinades, salad dressings, salad toppings, dips, breading, batter mixes, shelf stable spreads, barbecue sauces, liquid recipe mixes, concentrates, sauces or sauce mixes, including recipe mixes for salad, sold as a finished product or as an ingredient within a product, whether dehydrated, liquid or frozen.

The Beverage category means beverages, beverage mixes and concentrates, including but not limited to, carbonated and non-carbonated beverages, alcoholic and non-alcoholic beverages, ready to drink beverages, liquid concentrate formulations for preparing beverages such as sodas, and dry powdered beverage precursor mixes. The Beverage category also includes alcoholic drinks, soft drinks, sports drinks, isotonic beverages, and hot drinks. Alcoholic drinks include, but are not limited to beer, cider/perry, FABs, wine, and spirits. The soft drinks include, but are not limited to carbonates, such as colas and non-cola carbonates; fruit juice, such as juice, nectars, juice drinks and fruit flavored drinks; bottled water, which includes sparkling water, spring water and purified/table water, functional drinks, which can be carbonated or still and include sport, energy or elixir drinks; concentrates, such as liquid and powder concentrates in ready to drink measure. The drinks, either hot or cold, include, but are not limited to coffee or ice coffee, such as fresh, instant, and combined coffee; tea or ice tea, such as black, green, white, oolong, and flavored tea; and other drinks including flavor-, malt- or plant-based powders, granules, blocks or tablets mixed with milk or water.

The Snack Food category refers to any food that can be a light informal meal including, but not limited to, sweet and savory snacks and snack bars. Examples of snack food include, but are not limited to, fruit snacks, chips/crisps, extruded snacks, tortilla/corn chips, popcorn, pretzels, nuts and other sweet and savory snacks. Examples of snack bars include, but are not limited to, granola/muesli bars, breakfast bars, energy bars, fruit bars and other snack bars.

The Baked Goods category refers to any edible product the process of preparing which involves exposure to heat or excessive sunlight. Examples of baked goods include, but are not limited to bread, buns, cookies, muffins, cereal, toaster pastries, pastries, waffles, tortillas, biscuits, pies, bagels, tarts, quiches, cake, any baked foods, and any combination thereof.

The Ice Cream category refers to frozen dessert containing cream and sugar and flavoring. Examples of ice cream include, but are not limited to: impulse ice cream; take-home ice cream; frozen yoghurt and artisanal ice cream; soy, oat, bean (e.g., red bean and mung bean), and rice-based ice creams.

The Confectionary category refers to edible product that is sweet to the taste. Examples of confectionary include, but are not limited to, candies, gelatins, chocolate confectionery, sugar confectionery, gum, and the likes and any combination products.

The Meal Replacement category refers to any food intended to replace the normal meals, particularly for people having health or fitness concerns. Examples of meal replacement include, but are not limited to, slimming products and convalescence products.

The Ready Meal category refers to any food that can be served as a meal without extensive preparation or processing. The ready meal includes products that have had recipe “skills” added to them by the manufacturer, resulting in a high degree of readiness, completion and convenience. Examples of ready meals include, but are not limited to canned/preserved, frozen, dried, chilled ready meals; dinner mixes; frozen pizza; chilled pizza; and prepared salads.

The Pasta and Noodle category includes any pastas and/or noodles including, but not limited to canned, dried and chilled/fresh pasta; and plain, instant, chilled, frozen and snack noodles.

The Canned/Preserved Food category includes, but is not limited to, canned/preserved meat and meat products, fish/seafood, vegetables, tomatoes, beans, fruit, ready meals, soup, pasta, and other canned/preserved foods.

The Frozen Processed Food category includes, but is not limited to, frozen processed red meat, processed poultry, processed fish/seafood, processed vegetables, meat substitutes, processed potatoes, bakery products, desserts, ready meals, pizza, soup, noodles, and other frozen food.

The Dried Processed Food category includes, but is not limited to, rice, dessert mixes, dried ready meals, dehydrated soup, instant soup, dried pasta, plain noodles, and instant noodles. The Chill Processed Food category includes, but is not limited to, chilled processed meats, processed fish/seafood products, lunch kits, fresh cut fruits, ready meals, pizza, prepared salads, soup, fresh pasta and noodles.

The Sauces, Dressings and Condiments category includes, but is not limited to, tomato pastes and purees, bouillon/stock cubes, herbs and spices, monosodium glutamate (MSG), table sauces, soy based sauces, pasta sauces, wet/cooking sauces, dry sauces/powder mixes, ketchup, mayonnaise, mustard, salad dressings, vinaigrettes, dips, pickled products, and other sauces, dressings and condiments.

The Baby Food category includes, but is not limited to, milk- or soybean-based formula; and prepared, dried and other baby food.

The Spreads category includes, but is not limited to, jams and preserves, honey, chocolate spreads, nut based spreads, and yeast based spreads.

The Dairy Product category generally refers to edible product produced from mammal's milk. Examples of dairy product include, but are not limited to, drinking milk products, cheese, yoghurt and sour milk drinks, and other dairy products.

Additional examples for comestible composition, particularly food and beverage products or formulations, are provided as follows. Exemplary comestible compositions include one or more confectioneries, chocolate confectionery, tablets, countlines, bagged selflines/softlines, boxed assortments, standard boxed assortments, twist wrapped miniatures, seasonal chocolate, chocolate with toys, alfajores, other chocolate confectionery, mints, standard mints, power mints, boiled sweets, pastilles, gums, jellies and chews, toffees, caramels and nougat, medicated confectionery, lollipops, liquorice, other sugar confectionery, gum, chewing gum, sugarized gum, sugar-free gum, functional gum, bubble gum, bread, packaged/industrial bread, unpackaged/artisanal bread, pastries, cakes, packaged/industrial cakes, unpackaged/artisanal cakes, cookies, chocolate coated biscuits, sandwich biscuits, filled biscuits, savory biscuits and crackers, bread substitutes, breakfast cereals, rte cereals, family breakfast cereals, flakes, muesli, other cereals, children's breakfast cereals, hot cereals, ice cream, impulse ice cream, single portion dairy ice cream, single portion water ice cream, multi-pack dairy ice cream, multi-pack water ice cream, take-home ice cream, take-home dairy ice cream, ice cream desserts, bulk ice cream, take-home water ice cream, frozen yoghurt, artisanal ice cream, dairy products, milk, fresh/pasteurized milk, full fat fresh/pasteurized milk, semi skimmed fresh/pasteurized milk, long-life/uht milk, full fat long life/uht milk, semi skimmed long life/uht milk, fat-free long life/uht milk, goat milk, condensed/evaporated milk, plain condensed/evaporated milk, flavored, functional and other condensed milk, flavored milk drinks, dairy only flavored milk drinks, flavored milk drinks with fruit juice, soy milk, sour milk drinks, fermented dairy drinks, coffee whiteners, powder milk, flavored powder milk drinks, cream, cheese, processed cheese, spreadable processed cheese, unspreadable processed cheese, unprocessed cheese, spreadable unprocessed cheese, hard cheese, packaged hard cheese, unpackaged hard cheese, yoghurt, plain/natural yoghurt, flavored yoghurt, fruited yoghurt, probiotic yoghurt, drinking yoghurt, regular drinking yoghurt, probiotic drinking yoghurt, chilled and shelf-stable desserts, dairy-based desserts, soy-based desserts, chilled snacks, fromage frais and quark, plain fromage frais and quark, flavored fromage frais and quark, savory fromage frais and quark, sweet and savory snacks, fruit snacks, chips/crisps, extruded snacks, tortilla/corn chips, popcorn, pretzels, nuts, other sweet and savory snacks, snack bars, granola bars, breakfast bars, energy bars, fruit bars, other snack bars, meal replacement products, slimming products, convalescence drinks, ready meals, canned ready meals, frozen ready meals, dried ready meals, chilled ready meals, dinner mixes, frozen pizza, chilled pizza, soup, canned soup, dehydrated soup, instant soup, chilled soup, hot soup, frozen soup, pasta, canned pasta, dried pasta, chilled/fresh pasta, noodles, plain noodles, instant noodles, cups/bowl instant noodles, pouch instant noodles, chilled noodles, snack noodles, canned food, canned meat and meat products, canned fish/seafood, canned vegetables, canned tomatoes, canned beans, canned fruit, canned ready meals, canned soup, canned pasta, other canned foods, frozen food, frozen processed red meat, frozen processed poultry, frozen processed fish/seafood, frozen processed vegetables, frozen meat substitutes, frozen potatoes, oven baked potato chips, other oven baked potato products, non-oven frozen potatoes, frozen bakery products, frozen desserts, frozen ready meals, frozen pizza, frozen soup, frozen noodles, other frozen food, dried food, dessert mixes, dried ready meals, dehydrated soup, instant soup, dried pasta, plain noodles, instant noodles, cups/bowl instant noodles, pouch instant noodles, chilled food, chilled processed meats, chilled fish/seafood products, chilled processed fish, chilled coated fish, chilled smoked fish, chilled lunch kit, chilled ready meals, chilled pizza, chilled soup, chilled/fresh pasta, chilled noodles, oils and fats, olive oil, vegetable and seed oil, cooking fats, butter, margarine, spreadable oils and fats, functional spreadable oils and fats, sauces, dressings and condiments, tomato pastes and purees, bouillon/stock cubes, stock cubes, gravy granules, liquid stocks and fonds, herbs and spices, fermented sauces, soy based sauces, pasta sauces, wet sauces, dry sauces/powder mixes, ketchup, mayonnaise, regular mayonnaise, mustard, salad dressings, regular salad dressings, low fat salad dressings, vinaigrettes, dips, pickled products, other sauces, dressings and condiments, baby food, milk formula, standard milk formula, follow-on milk formula, toddler milk formula, hypoallergenic milk formula, prepared baby food, dried baby food, other baby food, spreads, jams and preserves, honey, chocolate spreads, nut-based spreads, and yeast-based spreads. Exemplary comestible compositions also include confectioneries, bakery products, ice creams, dairy products, sweet and savory snacks, snack bars, meal replacement products, ready meals, soups, pastas, noodles, canned foods, frozen foods, dried foods, chilled foods, oils and fats, baby foods, or spreads or a mixture thereof. Exemplary comestible compositions also include breakfast cereals, sweet beverages or solid or liquid concentrate compositions for preparing beverages, ideally so as to enable the reduction in concentration of previously known saccharide sweeteners, or artificial sweeteners.

Concentrates

According to another aspect of the invention, the compounds of the present invention can be provided in a concentrate formulation, e.g., suitable for subsequent processing to produce a ready-to-use (i.e., ready-to-serve) product.

By “a flavoring concentrate formulation,” is meant a formulation that can be reconstituted with one or more diluting media to become a ready-to-use composition. The term “ready-to-use composition” is used interchangeably herein with “ingestible composition,” which denotes any substance that, either alone or together with another substance, can be taken orally whether intended for consumption or not. In one embodiment, the ready-to-use composition includes a composition that can be directly consumed by a human or animal.

The flavoring concentrate formulation is typically used by mixing with one or more diluting media, e.g., any consumable or ingestible ingredient or product, to impart or modify one or more flavors to the diluting medium. Such a process is often referred to as reconstitution.

The reconstitution can be conducted in a household setting or an industrial setting. For example, a frozen fruit juice concentrate can be reconstituted with water or other aqueous medium by a consumer in a kitchen to obtain the ready-to-use fruit juice beverage. In another example, a soft drink syrup concentrate can be reconstituted with water or other aqueous medium by, for example, a restaurant, vendor, or a manufacturer in large industrial scale to produce the ready-to-use soft drinks.

Because the flavoring concentrate formulation has the flavoring agent or flavor modifying agent in a concentration higher than the ready-to-use composition, the flavoring concentrate formulation is typically not suitable for being consumed directly without reconstitution.

There are many benefits of using and producing a flavoring concentrate formulation. For example, one benefit is the reduction in weight and volume for transportation as the flavoring concentrate formulation can be reconstituted at the time of usage by the addition of suitable solvent, solid or liquid.

In one embodiment, the flavoring concentrate formulation comprises a compound of the present invention; a carrier, and optionally, at least one adjuvant. The term “as flavor modifying ingredient” denotes that the compound of the present invention acts as a flavoring agent or a flavor modifying agent (such as a flavor enhancer) in the formulation. The term “carrier” denotes a usually inactive accessory substance, such as solvents, binders, or other inert medium, which is used in combination with the present compound and one or more optional adjuvants to form the formulation. For example, water or starch can be a carrier for a flavoring concentrate formulation. In some embodiments, the carrier is the same as the diluting medium for reconstituting the flavoring concentrate formulation; and in other embodiments, the carrier is different from the diluting medium. The term “carrier” as used herein includes, but is not limited to, ingestibly acceptable carrier.

The term “adjuvant” denotes an additive that supplements, stabilizes, maintains, or enhances the intended function or effectiveness of the active ingredient, such as the compound of the present invention. In one embodiment, the at least one adjuvant comprises one or more flavoring agents. The flavoring agent may be of any flavor known to one skilled in the art or consumers, such as the flavor of chocolate, coffee, tea, mocha, French vanilla, peanut butter, chai, or combinations thereof. In another embodiment, the at least one adjuvant comprises one or more sweeteners. The one or more sweeteners can be any of the sweeteners described herein. In another embodiment, the at least one adjuvant comprises one or more ingredients selected from emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, salts, and combinations thereof. Examples of emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, and salts are described in U.S. Pat. No. 6,468,576, which is hereby incorporated by reference in its entirety.

The present flavoring concentrate formulation can be in a form selected from, for example, liquid including solution and suspension, solid, foamy material, paste, gel, cream, and a combination thereof, such as a liquid containing a certain amount of solid contents. In one embodiment, the flavoring concentrate formulation is in the form of a liquid, including aqueous-based and non-aqueous-based. The flavoring concentrate formulation can be carbonated or non-carbonated.

The flavoring concentrate formulation may further comprise a freezing point depressant, nucleating agent, or both as the at least one adjuvant. The freezing point depressant is a ingestibly acceptable compound or agent that can depress the freezing point of a liquid or solvent to which the compound or agent is added. That is, a liquid or solution containing the freezing point depressant has a lower freezing point than the liquid or solvent without the freezing point depressant. In addition to depressing the onset freezing point, the freezing point depressant may also lower the water activity of the flavoring concentrate formulation. Examples of freezing point depressants include, but are not limited to, carbohydrates, oils, ethyl alcohol, polyol, e.g., glycerol, and combinations thereof.

Nucleating agents are ingestibly acceptable compounds or agents that facilitate nucleation. The presence of a nucleating agent in the flavoring concentrate formulation can improve the mouthfeel of, for example, a frozen slush and help maintain the physical properties and performance of the slush at freezing temperatures by increasing the number of ice crystallization centers. Examples of nucleating agents include, but are not limited to, calcium silicate, calcium carbonate, titanium dioxide, and combinations thereof.

In one embodiment, the flavoring concentrate formulation is formulated to have a low water activity for extended shelf life. Water activity is the ratio of the vapor pressure of water in a formulation to the vapor pressure of pure water at the same temperature. In one embodiment, the concentrate formulation has a water activity of less than about 0.85. In another embodiment, the concentrate formulation has a water activity of less than about 0.80. In another embodiment, the concentrate formulation has a water activity of less than about 0.75.

In one embodiment, the flavoring concentrate formulation has the present compound in a concentration that is at least 2, 5, 10, 20, 30, 40, 50, 75, 100, or more times the concentration of the compound in a ready-to-use composition.

Having now generally described the invention, the same will be more readily understood by reference to the following examples, which are provided by way of illustration and are not intended as limiting. It is understood that various modifications and changes can be made to the herein disclosed exemplary embodiments without departing from the spirit and scope of the invention.

EXAMPLES Example 1—General Method for Measuring Taste Receptor Activity —Fluo-4 Calcium Assay

Fluo-4 is a fluorescent indicator for intracellular calcium and allows the determination of changes in calcium concentration, in particular an increase in response to receptor activation occurring after ligand addition. HEK293 cells stably expressing Gα16-gustducin 44 (Gα16gust44) were used as host cells and transfected with various constructs as described in examples 2-5. Black, clear-bottom 96-well plates were used for all assays. They were seeded the day before the assay with 8500 transfected cells per well and maintained at 37° C. overnight in a growth medium appropriate for the cells used. For HEK293 cells, Dulbecco's Modified Eagle medium supplemented with 10% fetal bovine serum was used for growth and maintenance of the HEK293 cells.

At the time of the assay, the growth medium was discarded and cells were incubated for 1 hour (at 37° C. in the dark) with 50 μl of a calcium assay solution consisting of 1.5 μM Fluo-4 AM (Molecular Probes™, Invitrogen, US) and 2.5 μM probenicid (Sigma-Aldrich) dissolved in a C1 buffer solution. C1 buffer solution contains 130 mM NaCl, 5 mM KCl, 10 mM Hepes, 2 mM CaCl₂ and 10 mM glucose (pH 7.4).

After the initial 1 hour loading period, the plates were washed 5 times with 100 μl per well of C1 buffer using an automated plate washer (BioTek) and after washing, the cells were further incubated in 100 μl C1 buffer per well for 30 minutes at room temperature in the dark to allow for complete de-esterification of the Fluo-4-AM. The buffer solutions were discarded, the plate was washed 5 times with 100 μl C wash buffer and finally the cells were placed in 180 μl of C1 wash buffer.

For assay reading, the plate was placed in a FLIPR (fluorescence imaging plate reader (FLIPR-Tetra, Molecular Devices), and receptor activation was initiated following addition of 20 μl of a 10× concentrated ligand stock solution. Fluorescence was continuously monitored for 15 seconds prior to ligand addition and for 105 seconds after ligand addition (45-105 sec may be sufficient).

Receptor activation is given in relative fluorescence units (RFU) and is defined by the following equation: Fluorescence Increase—Maximum Fluorescence—baseline fluorescence, wherein the baseline fluorescence represents the mean fluorescence calculated for the first 10 to 15 seconds prior to ligand addition.

Alternatively, Receptor activation is determined by the increase in peak fluorescence (F) normalized to the baseline fluorescence (F₀). The data are normalized using the following equation: ΔF/F=(F−F₀)/F₀, where F is the peak fluorescence signal and F₀ is the baseline fluorescence signal, wherein the baseline fluorescence represents the mean fluorescence calculated for the first 10 to 15 seconds prior to ligand addition.

As a negative control, mock transfected cells were exposed to the same concentration of ligand and the concentration of calcium traces not corresponding to a signal was determined. Cells with an activated receptor were identified by the signal (RFU or ΔF/F) being significantly above the negative control.

Example 2—Sweet Flavor and Sweet Flavor Enhancement Measurement Using Human Panelists Conducting a Paired Comparison Test

Test samples containing experimental compounds are presented in pairs to the panelist and they are asked to determine which of the samples is sweeter. The present compounds can be tested for sweet flavor enhancement in a medium with a wide range of pH values, for example, at pH of about 7.1 or about 2.8. A group of 10 to 16 or more panelists can participate in each test. Subjects refrain from eating or drinking (except water) for at least 1 hour prior to the test. Subjects rinse with water several times to clean the mouth prior to testing.

Taste tests were performed with sucrose or HFCS as the sweetener in the presence or absence of compound. A 0.2% stock solution of compound in water with sodium bicarbonate was prepared and then this stock solution was diluted in the final sample to achieve the targeted final concentration of compound. Taste samples were also prepared in a low sodium phosphate buffer (pH 7.1; “LSB”) lacking sucrose or HFCS to evaluate the taste of the compound alone.

Low sodium phosphate buffer consists of 0.3 mM KCl, 0.5 mM Na2HPO4, and 0.175 mM KH2PO4. Sample volumes are usually 20 ml.

In one paired comparison test, the panelist is presented with two different samples and asked to identify the sample which is sweeter. The samples within a paired comparison test are presented in a randomized, counterbalanced order. Panelists have up to a 1 minute delay between taste tests to clear the mouth of any tastes.

Binomial probability tables are used to determine the probability of the correct number of responses occurring for each test at alpha=0.05.

Example 3—Ranking Tests to Determine the Sweetness Isointensity of Sweetness Enhancers

For comparative ranking, samples of 0.5%, 1%, 1.5%, 7%, 8%, 9%, 10% and 11% sucrose solutions can be prepared.

a) Sweetness Isointensity of Sweetness Enhancer in Sucrose Solutions

The sensory evaluation can be conducted using a ranking method. Samples at ambient temperature can be randomly presented in 15 ml blind aliquots (unidentifiable by panelists). Panels consisting of 10 sweet sensitive subjects and samples can be presented in 3 replications over 1 session. After tasting each sample, the mouth is rinsed thoroughly with water at ambient temperature prior to tasting the next sample. Panelists can be presented with 7%, 8%, 9%, 10%, 11% sucrose samples and a sixth sample of 7% sucrose with a sweetness enhancer in a concentration near its sweetness detection threshold. They can be asked to rank the samples from low to high with respect to perceived sweet taste. R-indices can be calculated for 7% sucrose with the sweetness enhancer versus 7%, 8%, 9%, 10% or 11% sucrose.

b) Near Threshold Sweetness Isointensity of Sweetness Enhancer in Water

The sensory evaluation can be conducted using a ranking method. Samples at ambient temperature can be randomly presented in 15 ml blind aliquots (unidentifiable by panelists). Panels consisting of 10 sweet sensitive subjects and samples can be presented in 3 replications over 1 session. After tasting each sample, the mouth is rinsed thoroughly with water at ambient temperature prior to tasting the next sample.

Panelists can be presented with either 0.5% and 1% sucrose or 1% and 1.5% sucrose and a third sample of water with a sweetness enhancer in a concentration near its sweetness detection threshold. They can be asked to rank the samples from low to high with respect to perceived sweet taste.

R-indices can be calculated for the sweetness enhancer in water versus either 0.5% and 1% sucrose or 1% and 1.5% sucrose. The R-index is a statistic obtained by an analytical procedure based on signal detection and is a short-cut method for determining the proportion of subjects choosing one sample over another (see O'Mahony, 1992, J. Sens. Stud., 7:1-47). From ranking-style sensory tests, a matrix of responses (see table 2 below) is constructed such that each cell contains the number of times a given sample was ranked at a particular location.

TABLE 2 Position 1 Position 2 Sample (least sweet) (most sweet) Position 3 Sample X A B C Sample Y D E F Sample Z G H I From this matrix, the R-index can be calculated according to the following equation:

R−index(X vs. Y)=A(E+F)+B(F)+0.5((A*D)+(B*E)+(C*F))(A+B+C)*(D+E+F).

Essentially, the R-index is a measure of difference between two samples. The R-index has a chance level of detection of 50%. Thus, when comparing two samples, the derived R-index must be significantly different from 50% in order for them to be considered different. The critical value is the statistically relevant value that the derived R-index must deviate from (i.e., greater or less than) in order to be considered significant.

An R-index greater than the higher critical value means that the sweetness enhancer sample is significantly sweeter than the sucrose sample. An R-index not significantly different from the critical value means that the sweetness enhancer sample has an equivalent sweetness to the compared sucrose sample. An R-index below the lower critical value indicates that the sucrose sample is sweeter than the sweetness enhancer sample.

All patents, patent applications, provisional applications, and publications referred to or cited herein are incorporated by reference in their entirety, including all figures and tables, to the extent they are not inconsistent with the explicit teachings of this specification.

It should be understood that the examples and embodiments described herein are for illustrative purposes only and that various modifications or changes in light thereof will be suggested to persons skilled in the art and are to be included within the spirit and purview of this application.

TABLE 1 NAME (if Present SMILES STRUCTURE available) In CC(C)CC(═O)OCCC(C)CCCC(C)═C Rhodinyl isovalerate CCC(═O)OC\C═C(\C)CCC═C(C)C Neryl propio-te FooDB CCCCCCCCCCCCC1CCC(═O)O1 5-Dodecyldihydro- FooDB 2(3H)-furanone OCC(O)C(O)CO D-Threitol FooDB NC1═NC═NC2═C1N═CN2[C@@H]1O[C@@H]2COP(O)(═O)O[C@H]2 Cyclic AMP FooDB [C@H]1O OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O D-Galactose FooDB O1C═CC═C1C1═CC═CS1 2-(2-Thienyl)furan FooDB COC1═CC2═C(NC═C2CCNC(C)═O)C═C1 Melatonin FooDB [O−]P([O−])(═O)OP([O−])([O−])═O Pyrophosphate FooDB C\C(CCC═C)═C/CC[C@](C)(O)C═C (3S,6E)-Nerolidol FooDB CCCC\C═C/CCOC(═O)CC cis-3-Octenyl FooDB propio-te CC1═COC2═C1C(═O)C1C(C)(O)CCC(O)C1(C)C2 Curcolonol FooDB CN(C)C(═N)NCCC[C@H](N)C(O)═O \NG,NG-Dimethyl- FooDB L-arginine\ [H]OC1([H])C([H])([H])OC(═O)C([H])([H])C([H])([H])C1([H])O[H] Solerol FooDB OC[C@@]1(O)CO[C@@H](OC[C@H]2O[C@@H](OC3═CC4═C(C(O)═ Apigenin 7-apiosyl- FooDB C3)C(═O)C═C(O4)C3═CC═C(O)C═C3)[C@H](O)[C@@H](O)[C@@H]2 glucoside O)[C@@H]1O [H]OC([H])(C(═O)N([H])C([H])([H])C([H])([H])C(═O)N([H])C([H])([H])C([H]) \3a,7a,12a,24- FooDB ([H])SC(═O)C([H])(C([H])([H])[H])C([H])(O[H])C([H])([H])C([H])([H])C([H]) Tetrahydroxy-5b- (C([H])([H])[H])C1([H])C([H])([H])C([H])([H])C2([H])C3([H])[C@]([H])(O[H]) cholestanoyl-CoA\ C([H])([H])[C@]4([H])C([H])([H])[C@]([H])(O[H])C([H])([H])C([H])([H])C4 (C([H])([H])[H])C3([H])C([H])([H])[C@]([H])(O[H])C12C([H])([H])[H])C(C([H]) ([H])[H])(C([H])([H])[H])C([H])([H])OP(═O)(O[H])OP(═O)(O[H])OC([H]) ([H])[C@@]1([H])O[C@@]([H])(N2C([H])═NC3═C2N═C([H])N═C3N([H])[H]) [C@]([H])(O[H])[C@]1([H])OP(═O)(O[H])O[H] [H]OC([H])(C(═O)N([H])C([H])([H])C([H])([H])C(═O)N([H])C([H])([H])C([H]) \3a,7a,12a- FooDB ([H])SC(═O)C([H])(C(═O)C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C1 Trihydroxy-5b-24- ([H])C([H])([H])C([H])([H])[C@@]2([H])C3([H])[C@]([H])(O[H])C([H])([H])[C oxocholestanoyl- @]4([H])C([H])([H])[C@]([H])(O[H])C([H])([H])C([H])([H])C4(C([H])([H])[H]) CoA\ [C@@]3([H])C([H])([H])[C@]([H])(O[H])C12C([H])([H])[H])C([H])([H])[H]) C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])OP(═O)(O[H])OP(═O)(O[H])OC ([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])═NC3═C2N═C([H])N═C3N ([H])[H])[C@]([H])(O[H])[C@]1([H])OP(═O)(O[H])O[H] [H]O[C@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@@]([H]) \3a,7a-Dihydroxy- FooDB (C1([H])[H])C([H])([H])[C@@]([H])(O[H])[C@@]1([H])[C@]3([H])C([H])([H]) 5b-cholestane\ C([H])([H])[C@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H]) ([H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]3(C([H])([H])[H])C([H])([H]) C([H])([H])[C@]21[H] [H]O[C@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])C([H])(C1([H]) \3a,7a-Dihydroxy- FooDB [H])C([H])([H])[C@@]([H])(O[H])C1([H])C3([H])C([H])([H])C([H])([H])C 5b-cholestan-26-al\ ([H])(C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])═O) C([H])([H])[H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])C21[H] [H]OC(═O)C([H])([H])N([H])C(═O)C([H])(N([H])[H])C([H])([H])[H] Alanylglycine FooDB [H]OC([H])(C(═O)N([H])C([H])([H])C([H])([H])C(═O)N([H])C([H])([H])C([H]) \3a,7a-Dihydroxy- FooDB ([H])SC(═O)C(═C([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C1([H]) 5b-cholest-24- C([H])([H])C([H])([H])C2([H])C3([H])[C@]([H])(O[H])C([H])([H])[C@]4([H]) enoyl-CoA\ C([H])([H])[C@]([H])(O[H])C([H])([H])C([H])([H])[C@]4(C([H])([H])[H])C3 ([H])C([H])([H])C([H])([H])[C@]12C([H])([H])[H])C([H])([H])[H])C(C([H])([H]) [H])(C([H])([H])[H])C([H])([H])OP(═O)(O[H])OP(═O)(O[H])OC([H])([H])[C@ @]1([H])O[C@@]([H])(N2C([H])═NC3═C2N═C([H])N═C3N([H])[H])[C@] ([H])(O[H])[C@]1([H])OP(═O)(O[H])O[H] [H]OC([H])(C(═O)N([H])C([H])([H])C([H])([H])C(═O)N([H])C([H])([H])C([H]) \3a,7a-Dihydroxy- FooDB ([H])SC(═O)C([H])(C(═O)C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C1([H]) 5b-24- C([H])([H])C([H])([H])C2([H])C3([H])[C@]([H])(O[H])C([H])([H])[C@]4 oxocholestanoyl- ([H])C([H])([H])[C@]([H])(O[H])C([H])([H])C([H])([H])[C@]4(C([H])([H])[H])C CoA\ 3([H])C([H])([H])C([H])([H])[C@]12C([H])([H])[H])C([H])([H])[H])C(C([H]) ([H])[H])(C([H])([H])[H])C([H])([H])OP(═O)(O[H])OP(═O)(O[H])OC([H])([H]) [C@@]1([H])O[C@@]([H])(N2C([H])═NC3═C2N═C([H])N═C3N([H])[H])[C @]([H])(O[H])[C@]1([H])OP(═O)(O[H])O[H] [H]OC1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(═O)(O[H])OP(═O)(O \CDP- FooDB [H])OC([H])([H])[C@]([H])(OC(═O)C([H])([H])C([H])([H])C([H])([H])C([H]) DG(16:0/18:2(9Z,12Z))\ ([H])C([H])([H])C([H])([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])═C([H])C ([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])OC(═O) C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H]) C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H]) C([H])([H])[H])[C@]1([H])O[H])N1C([H])═C([H])C(═NC1═O)N([H])[H] [H]OC1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(═O)(O[H])OP(═O)(O \CDP- FooDB [H])OC([H])([H])[C@]([H])(OC(═O)C([H])([H])C([H])([H])C([H])([H])C([H])═ DG(16:0/20:4(5Z,8Z, C([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])═C 11Z,14Z))\ ([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])O C(═O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C ([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C ([H])([H])C([H])([H])[H])[C@]1([H])O[H])N1C([H])═C([H])C(═NC1═O)N([H]) [H] [H]OC1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(═O)(O[H])OP(═O)(O \CDP- FooDB [H])OC([H])([H])[C@]([H])(OC(═O)C([H])([H])C([H])([H])C([H])([H])C([H]) DG(16:0/20:4(8Z,11Z, ([H])C([H])([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])═C([H])C([H])([H])C 14Z,17Z))\ ([H])═C([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])([H])[H])C([H])([H])O C(═O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C ([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C ([H])([H])C([H])([H])[H])[C@]1([H])O[H])N1C([H])═C([H])C(═NC1═O)N([H]) [H] [H]OC1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(═O)(O[H])OP(═O)(O \CDP- FooDB [H])OC([H])([H])[C@]([H])(OC(═O)C([H])([H])C([H])([H])C([H])([H])C([H]) DG(18:0/18:2(9Z,12Z))\ ([H])C([H])([H])C([H])([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])═C([H])C ([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])OC(═O) C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H]) C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H]) C([H])([H])C([H])([H])C([H])([H])[H])[C@]1([H])O[H])N1C([H])═C([H])C(═N C1═O)N([H])[H] [H]OC1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(═O)(O[H])OP(═O)(O \CDP- FooDB [H])OC([H])([H])[C@]([H])(OC(═O)C([H])([H])C([H])([H])C([H])([H])C([H])═ DG(18:0/20:4(5Z,8Z, C([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])═C 11Z,14Z))\ ([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])O C(═O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C ([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C ([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@]1([H])O[H])N1C([H])═C ([H])C(═NC1═O)N([H])[H] [H]OC(═O)C1═C([H])N═C(C(O[H])═C1C(═O)O[H])C([H])([H])[H] \3-Hydroxy-2- FooDB methylpyridine-4,5- dicarboxylate\ [H]OC1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(═O)(O[H])OP(═O)(O \CDP- FooDB [H])OC([H])([H])[C@]([H])(OC(═O)C([H])([H])C([H])([H])C([H])([H])C([H]) DG(16:0/22:3(10Z, ([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])═ 13Z,16Z))\ C([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H]) C([H])([H])[H])C([H])([H])OC(═O)C([H])([H])C([H])([H])C([H])([H])C([H])([H]) C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H]) ([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@]1([H])O[H])N1C([H])═ C([H])C(═NC1═O)N([H])[H] [H]OC1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(═O)(O[H])OP(═O)(O \CDP- FooDB [H])OC([H])([H])[C@]([H])(OC(═O)C([H])([H])C([H])([H])C([H])═C([H])C([H]) DG(16:0/22:6(4Z,7Z, ([H])C([H])═C([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])═C([H])C([H]) 10Z,13Z,16Z,19Z))\ ([H])C([H])═C([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])([H])[H])C([H])([H]) OC(═O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H]) C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H]) C([H])([H])[H])[C@]1([H])O[H])N1C([H])═C([H])C(═NC1═O)N ([H])[H] [H]OC1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(═O)(O[H])OP(═O)(O \CDP- FooDB [H])OC([H])([H])[C@]([H])(OC(═O)C([H])([H])C([H])([H])C([H])([H])C([H]) DG(18:0/20:4(8Z,11Z, ([H])C([H])([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])═C([H])C([H])([H])C 14Z,17Z))\ ([H])═C([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])([H])[H])C([H])([H])O C(═O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C ([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C ([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@]1([H])O[H])N1C([H])═C ([H])C(═NC1═O)N([H])[H] [H]OC1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(═O)(O[H])OP(═O)(O \CDP- FooDB [H])OC([H])([H])[C@]([H])(OC(═O)C([H])([H])C([H])([H])C([H])([H])C([H]) DG(18:0/22:3(10Z, ([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])═ 13Z,16Z))\ C([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H]) C([H])([H])[H])C([H])([H])OC(═O)C([H])([H])C([H])([H])C([H])([H])C([H]) ([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H]) C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]) [C@]1([H])O[H])N1C([H])═C([H])C(═NC1═O)N([H])[H] COC1═C(CC(OO)C(C)═C)C(O)═C(C═C1)C(═O)\C═C\C1═CC═C(O)C═C1 Xanthoangelol E FooDB COC1═CC═C(C(═O)\C═C\C2═CC═C(O)C═C2)C(O)═C1CC(O)C(C)═C Xanthoangelol D FooDB OCC(CO)OC═O Monoacyl glycerol FooDB [H]OC(═O)C([H])([H])C([H])([H])C([H])([H])C(\[H])═C(\[H])C([H])([H])C(\[H])═ 12S-HHT FooDB C(/[H])\C(\[H])═C(/[H])[C@@]([H])(O[H])C([H])([H])C([H])([H])C([H])([H]) C([H])([H])C([H])([H])[H] [H]OC([H])(C(═O)N([H])C([H])([H])C([H])([H])C(═O)N([H])C([H])([H])C([H]) \2,4,7,10,13,16,19- FooDB ([H])SC(═O)C([H])═C([H])C([H])═C([H])C([H])([H])C([H])═C([H])C([H])([H]) Docosaheptaenoyl- C([H])═C([H])C([H])([H])C([H])═C([H])C([H])([H])C([H])═C([H])C([H])([H]) CoA\ C([H])═C([H])C([H])([H])C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C ([H])([H])OP(═O)(O[H])OP(═O)(O[H])OC([H])([H])[C@@]1([H])O[C@@]([H]) (N2C([H])═NC3═C2N═C([H])N═C3N([H])[H])[C@]([H])(O[H])[C@]1([H]) OP(═O)(O[H])O[H] [H]OC1([H])C([H])([H])C2(OC2(C([H])([H])C(═O)C(═C([H])C([H])═C([H])C Fucoxanthin FooDB (═C([H])C([H])═C([H])C([H])═C(C([H])═C([H])C([H])═C(C([H])═C═C2C(O [H])(C([H])([H])[H])C([H])([H])C([H])(OC(═O)C([H])([H])[H])C([H])([H])C2(C ([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C ([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C1([H])[H])C([H])([H])[H] [H]OC1═NC(═NC(N([H])[H])═C1N(C([H])═O)C([H])([H])[H])N([H])[H] \2,6-Diamino-4- FooDB hydroxy-5-N- methylformamidopyrimidine\ CC(C)C1CCC(C)C═C1O cis-p-Menth-2-enol FooDB [H]OC([H])(C(═O)N([H])C([H])([H])C([H])([H])C(═O)N([H])C([H])([H])C([H]) \Cyclohex-1,5- FooDB ([H])SC(═O)C1═C([H])C([H])([H])C([H])([H])C([H])═C1[H])C(C([H])([H])[H]) diene-1-carboxyl- (C([H])([H])[H])C([H])([H])OP(═O)(O[H])OP(═O)(O[H])OC([H])([H])[C@ CoA\ @]1([H])O[C@@]([H])(N2C([H])═NC3═C2N═C([H])N═C3N([H])[H])[C@] ([H])(O[H])[C@]1([H])OP(═O)(O[H])O[H] [H]OC([H])([H])[C@@]1([H])O[C@]([H])(OC([H])([H])C(═C([H])C([H])([H]) cis-Zeatin-O- FooDB N([H])C2═NC([H])═NC3═C2N([H])C([H])═N3)C([H])([H])[H])[C@]([H])(O glucoside [H])[C@@]([H])(O[H])[C@]1([H])O[H] CCCCCCCCCCCCCC(═O)SCCNC(═O)CCNC(═O)C(O)C(C)(C)COP(O) Tetradecanoyl-CoA HMDB (═O)OP(O)(═O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)═O)N1 C═NC2═C1N═CN═C2N NC1═NC(═O)C2═C(NCC(CN(C═O)C3═CC═C(C═C3)C(═O)N[C@@H](C 10- HMDB CC(O)═O)C(O)═O)N2)N1 Formyltetrahydrofolate O[C@@H]1[C@@H](COP(O)(═O)OP(O)(O)═O)OC([C@@H]1O)N1C═N IDP HMDB C2═C1NC═NC2═O NCC(═O)CCC(O)═O 5-Aminolevulinic HMDB acid OC[C@H]1O[C@H](O[C@H]2O[C@H](COP(O)(O)═O)[C@@H](O)[C@ Trehalose 6- HMDB H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O phosphate CC[C@](O)(C(C)═O)C(O)═O (S)-2-Aceto-2- HMDB hydroxybutanoic acid [H][C@@]1(CC═C2C3═C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@ Delta 8,14-Sterol HMDB H](C)[C@]1([H])CC3)[C@H](C)CCC(═C)C(C)C CC[C@](O)(C(C)═O)C(O)═O (S)-2-Aceto-2- HMDB hydroxybutanoic acid NC1═NC2═C(N═CN2[C@@H]2O[C@H](COP(O)(═O)OP(O)(═O)O[C@H] Guanosine HMDB 3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O) diphosphate C(═O)N1 mannose O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)═O)N1C(═O)NC Orotidylic acid HMDB (═O)C═C1C(O)═O O[C@@H]1[C@H](O)[C@@H](OP(O)(O)═O)[C@H](OP(O)(O)═O)[C@ Inositol 1,4,5- HMDB @H](O)[C@@H]1OP(O)(O)═O trisphosphate C[C@H](N)C(O)═O L-Alanine HMDB [H][C@@]12CCC([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2═ 3-beta-Hydroxy-4- HMDB CC[C@]2([H])[C@]1(C)CC[C@H](O)[C@@]2(C)C(O)═O beta-methyl-5- alpha-cholest-7- ene-4-alpha- carboxylate NC(CCC1═NC═C(C[C@H](N)C(O)═O)N1)C(O)═O 2-(3-Carboxy-3- HMDB aminopropyl)-L- histidine NC(N)═NCCCC(O)═O 4- HMDB Guanidinobutanoic acid OC(═O)[C@@H]1CC(═O)NC(═O)N1 L-Dihydroorotic HMDB acid CC1═CC2═C(C═C1C)N═CN2 Dimethylbenzimidazole HMDB OC(═O)CCCCCCC(═O)NCC(O)═O Suberylglycine HMDB N[C@@H](CC1═CC═C(O)C═C1)C(═O)N1CCC[C@H]1C(═O)N[C@@H] Endomorphin-1 HMDB (CC1═CNC2═CC═CC═C12)C(═O)N[C@@H](CC1═CC═CC═C1)C(N)═O OC1C2(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C41Cl Chlordecone HMDB alcohol OC(═O)CCCNCCC(O)═O N-Carboxyethyl-g- HMDB aminobutyric acid [H][C@@]12CC[C@@](O)(C(═O)CO)[C@@]1(C)C[C@H](O)[C@@]1 Cortisol HMDB ([H])[C@@]2([H])CCC2═CC(═O)CC[C@]12C OC[C@H]1O[C@@H](O[C@@H]2CO[C@@H](O)[C@H](O)[C@H]2O) Galactose-beta- HMDB [C@H](O)[C@@H](O)[C@H]1O 1,4-xylose CCCCC(C)C(═O)SCCNC(═O)CCNC(═O)C(O)C(C)(C)COP(O)(═O)OP(O) 2-Methylhexanoyl- HMDB (═O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)═O)N1C═NC2═ CoA C1N═CN═C2N O[C@H]1[C@H](OP(O)(O)═O)[C@@H](OP(O)(O)═O)[C@@H](O)[C@ 1D-Myo-inositol HMDB @H](OP(O)(O)═O)[C@@H]1OP(O)(O)═O 1,3,4,6- tetrakisphosphate O[C@@H]1C═C[C@@H](NCC2═CNC3═C2C(═O)NC(═N)N3)[C@@H]1O Queuine HMDB O[C@@H]1COC(═O)[C@H](O)[C@H]1O D-Xylono-1,5- HMDB lactone CCCCCCCC\C═C/CC(═O)SCCNC(═O)CCNC(═O)[C@H](O)C(C)(C)CO 3Z-dodecenoyl- HMDB P(O)(═O)OP(O)(═O)OC[C@H]1O[C@H](C(O)[C@H]1OP(O)(O)═O)N1C═ CoA NC2═C(N)N═CN═C12 CC(═O)C(═O)[C@H](N)[C@@H](O)[C@@H](OS(═O)(═O)O[C@@H]1[C Uridine HMDB @@H](COP(O)(═O)OP(O)(O)═O)O[C@H]([C@@H]1O)N1C═CC(═O)NC diphosphate 1═O)[C@H](O)CO acetylgalactosamine 4-sulfate OC1═NC2N═CN═CC2N1 8-Hydroxypurine HMDB CC(N)C(═O)NCC(O)═O Alanyl-Glycine HMDB OC(═O)C(\O)═C\C1═CC═C(O)C═C1 2-Hydroxy-3-(4- HMDB hydroxyphenyl)propenoic acid COC1═C(O)C═C2[C@H](CC3═CC(O)═C(O)C═C3)N(C)CCC2═C1 (S)-3-Hydroxy-N- HMDB methylcoclaurine C[C@@H](CCC═C(C)C)C1CCC2C3═C(CC[C@]12C)[C@@]1(C)CC[C 4a- HMDB @H](O)[C@](C)(C1CC3)C(O)═O Methylzymosterol- 4-carboxylic acid N[C@@H](CCCC(═O)OP(O)(═O)OCC1OC([C@H](O)[C@@H]1O)N1C═ L-2-Aminoadipate HMDB NC2═C(N)N═CN═C12)C(O)═O adenylate [H][C@@](COC(═O)CCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)O CDP- HMDB C[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCCCC DG(16:0/18:2(9Z,12Z)) CC\C═C/C\C═C/CCCCC [H][C@@](COC(═O)CCCCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O) CDP- HMDB OC[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCC DG(18:0/18:2(9Z,12Z)) CCCC\C═C/C\C═C/CCCCC CC(C)CCCC(C)C1CCC2C3[C@@H](O)CC4CC(═O)CC[C@]4(C)C3CC 7a-Hydroxy-5b- HMDB [C@]12C cholestan-3-one [H][C@@](COC(═O)CCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)OC CDP-DG(16:0/16:0) HMDB [C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCCCC CCCCCCCCCC [H][C@@](COC(═O)CCCCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O) CDP-DG(18:0/16:0) HMDB OC[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCC CCCCCCCCCCCC OC(C═O)C(O)═O Tartro-te HMDB semialdehyde CC1═NC═C(C═O)C(C(O)═O)═C1O 2-Methyl-3- HMDB hydroxy-5- formylpyridine-4- carboxylate CC1═NC═C(C(O)═O)C(C(O)═O)═C1O 3-Hydroxy-2- HMDB methylpyridine-4,5- dicarboxylate [H][C@@](COC(═O)CCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)O CDP- HMDB C[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCC\C═ DG(16:0/20:4(5Z,8Z, C/C\C═C/C\C═C/C\C═C/CCCCC 11Z,14Z)) [H][C@@](COC(═O)CCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)O CDP- HMDB C[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCCCC DG(16:0/20:4(8Z,11Z, C\C═C/C\C═C/C\C═C/C\C═C/CC 14Z,17Z)) [H][C@@](COC(═O)CCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)O CDP- HMDB C[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCCCC DG(16:0/22:3(10Z, CCC\C═C/C\C═C/C\C═C/CCCCC 13Z,16Z)) [H][C@@](COC(═O)CCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)O CDP- HMDB C[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CC\C═C DG(16:0/22:6(4Z,7Z, /C\C═C/C\C═C/C\C═C/C\C═C/C\C═C/CC 10Z,13Z,16Z,19Z)) [H][C@@](COC(═O)CCCCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O) CDP- HMDB OC[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCC\ DG(18:0/20:4(5Z,8Z, C═C/C\C═C/C\C═C/C\C═C/CCCCC 11Z,14Z)) [H][C@@](COC(═O)CCCCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O) CDP- HMDB OC[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCC DG(18:0/20:4(8Z,11Z, CCC\C═C/C\C═C/C\C═C/C\C═C/CC 14Z,17Z)) [H][C@@](COC(═O)CCCCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O) CDP- HMDB OC[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCC DG(18:0/22:3(10Z, CCCCC\C═C/C\C═C/C\C═C/CCCCC 13Z,16Z)) OC(═O)C(\O)═C\C1═CC═C(O)C═C1 2-Hydroxy-3-(4- HMDB hydroxyphenyl)propenoic acid COC1═C(O)C═C2[C@H](CC3═CC(O)═C(O)C═C3)N(C)CCC2═C1 (S)-3-Hydroxy-N- HMDB methylcoclaurine C[C@@H](CCC═C(C)C)C1CCC2C3═C(CC[C@]12C)[C@@]1(C)CC[C 4a- HMDB @H](O)[C@](C)(C1CC3)C(O)═O Methylzymosterol- 4-carboxylic acid [H][C@@](COC(═O)CCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)O CDP-DG(16:0/18:0) HMDB C[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCCCC CCCCCCCCCCCC [H][C@@](COC(═O)CCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)O CDP- HMDB C[C@H]1O[C@H]([C@@H](O)C1O)N1C═CC(N)═NC1═O)OC(═O)CCC DG(16:0/18:1(11Z)) CCCCCC\C═C/CCCCCC [H][C@@](COC(═O)CCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)O CDP- HMDB C[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCC DG(16:0/18:1(9Z)) CCCC\C═C/CCCCCCCC [H][C@@](COC(═O)CCCCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)O CDP-DG(18:0/18:0) HMDB C[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCC CCCCCCCCCCCCCC [H][C@@](COC(═O)CCCCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)O CDP- HMDB C[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCC DG(18:0/18:1(11Z)) CCCCCC\C═C/CCCCCC [H][C@@](COC(═O)CCCCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O) CDP- HMDB OC[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCC DG(18:0/18:1(9Z)) CCCC\C═C/CCCCCCCC CCCCC\C═C/C═C/C(CCCCCCCC(O)═O)OO 9(S)-HPODE HMDB [H][C@@](COC(═O)CCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)O CDP-DG(16:0/18:0) HMDB C[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCCCC CCCCCCCCCCCC [H][C@@](COC(═O)CCCCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O) CDP-DG(18:0/18:0) HMDB OC[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCC CCCCCCCCCCCCCC [H][C@@](COC(═O)CCCCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O) CDP- HMDB OC[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CC\C═ DG(18:0/22:6(4Z,7Z, C/C\C═C/C\C═C/C\C═C/C\C═C/C\C═C/CC 10Z,13Z,16Z,19Z)) [H][C@@](COC(═O)CCCCCCCCC\C═C/CCCCCC)(COP(O)(═O)OP(O) CDP- HMDB (═O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)C DG(18:1(11Z)/16:0) CCCCCCCCCCCCCC [H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)C(CCC3C1[C@H] Chenodeoxyglycocholoyl- HMDB (O)C2)C(C)CCC(═O)SCCNC(═O)CCNC(═O)C(O)C(C)(C)COP(O)(═O)OP CoA (O)(═O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)═O)N1C═NC2 ═C1N═CN═C2N CC(CCC(═O)NCC(O)═O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@] Chenodeoxyglycocholic HMDB 4(C)C3CC[C@]12C acid OC(C═O)C(O)═O Tartro-te HMDB semialdehyde [H][C@@](COC(═O)CCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)O CDP- HMDB C[C@H]1O[C@H]([C@@H](O)C1O)N1C═CC(N)═NC1═O)OC(═O)CCC DG(16:0/18:1(11Z)) CCCCCC\C═C/CCCCCC [H][C@@](COC(═O)CCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O)O CDP- HMDB C[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCCCC DG(16:0/18:1(9Z)) CC\C═C/CCCCCCCC [H][C@@](COC(═O)CCCCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O) CDP- HMDB OC[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCC DG(18:0/18:1(11Z)) CCCCCC\C═C/CCCCCC [H][C@@](COC(═O)CCCCCCCCCCCCCCCCC)(COP(O)(═O)OP(O)(═O) CDP- HMDB OC[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)CCC DG(18:0/18:1(9Z)) CCCC\C═C/CCCCCCCC [H][C@@](COC(═O)CCCCCCCCC\C═C/CCCCCC)(COP(O)(═O)OP(O) CDP- HMDB (═O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)C DG(18:1(11Z)/18:0) CCCCCCCCCCCCCCCC [H][C@@](COC(═O)CCCCCCCCC\C═C/CCCCCC)(COP(O)(═O)OP(O) CDP- HMDB (═O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C═CC(N)═NC1═O)OC(═O)C DG(18:1(11Z)/18:1 CCCCCCCC\C═C/CCCCCC (11Z)) CC1═NC═C(C═O)C(C(O)═O)═C1O 2-Methyl-3- HMDB hydroxy-5- formylpyridine-4- carboxylate C[C@@H]1OC(OCC(O)[C@@H](O)[C@H](O)[C@@H](NC(C)═O)C═O) N-Acetyl-6-O-L- HMDB [C@@H](O)[C@H](O)[C@@H]1O fucosyl-D- glucosamine [H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C 5a-Androstane- HMDB C[C@@]2([H])C[C@H](O)CC[C@]12C 3a,17a-diol OC(═O)C\C═C\CC(O)═O 3-Hexenedioic acid HMDB CCCCCCCCCCCCCCCCCCCCCCCCC(═O)N[C@@H](CO[C@@H]1O Glucosylceramide HMDB [C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)\C═C\CCCCCCCC (d18:1/25:0) CCCCC CCCCCCCCCCCCC(O)C(O)═O 2-Hydroxymyristic HMDB acid NC1═NC2═C(N(C═N)C(CNC3═CC═C(C═C3)C(═O)NC(CCC(O)═O)C(O)═ 5- HMDB O)CN2)C(═O)N1 Formiminotetrahydrofolic acid NC(N)═NCCCC(═O)C(O)═O 2-Oxoarginine HMDB CN(CC(O)═O)C(═N)NP(O)(O)═O Phosphocreatine HMDB OC[C@H]1O[C@@H](O)[C@H](NS(O)(═O)═O)[C@@H](O)[C@@H]1O N-Sulfo-D- HMDB glucosamine C[C@@H](N)C(═O)N[C@H](C)C(O)═O D-Alanyl-D-alanine HMDB CCCCCCCCC[C@H](O)CC(═O)SCCNC(═O)CCNC(═O)C(O)C(C)(C)CO (S)-3- HMDB P(O)(═O)OP(O)(═O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)═ Hydroxydodecanoyl- O)N1C═NC2═C(N)N═CN═C12 CoA OC(═O)C(═O)CC1═CC(O)═CC═C1 3- HMDB Hydroxyphenylpyruvic acid CC\C═C\CC(═O)SCCNC(═O)CCNC(═O)C(O)C(C)(C)COP(O)(═O)OP(O) trans-3-Hexenoyl- HMDB (═O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)═O)N1C═NC2═C CoA (N)N═CN═C12 CC(C)(COP(O)(═O)OP(O)(═O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1 Phenylacetyl-CoA HMDB OP(O)(O)═O)N1C═NC2═C(N)N═CN═C12)[C@@H](O)C(═O)NCCC(═O) NCCSC(═O)CC1═CC═CC═C1 CN1C(N)═NC2═C(NC═N2)C1═O 1-Methylguanine HMDB OC[C@H]1OC([C@@H](O)[C@@H]1O)N1C═NC2═C1NC═NC2═O Arabinosylhypoxanthine HMDB C═C1C═NC2═CC═CC═C12 3-Methylene- HMDB indolenine C\C(\C═C\C═C(/C)\C═C\C1C(C)═CC(═O)CC1(C)C)═C/C═C/C═C(\C)/C═ E,e-Carotene-3,3′- HMDB C/C═C(\C)/C═C/C1C(C)═CC(═O)CC1(C)C dione CC1═C2CC3═C(CCC(O)═O)C(C)═C(CC4═C(CCC(O)═O)C(C)═C(CC5═ Coproporphyrinogen I HMDB C(CCC(O)═O)C(C)═C(CC(N2)═C1CCC(O)═O)N5)N4)N3 CCCCC[C@H](O)\C═C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C═C/CC Thromboxane B2 HMDB CC(O)═O OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3 Maltopentaose HMDB [C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H] (O[C@H]5[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]5CO)O[C@@H] 4CO)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O CCCCCCCCCCCCCCCCCCCCCCCCC(O)C(═O)NC(COP(O)(═O)OC1 Mannosyl- HMDB C(O)C(O)C(OC2OC(CO)C(OP(O)(═O)OC3C(O)C(O)C(O)C(O)C3O)C(O) diinositol- C2O)C(O)C1O)C(O)C(O)CCCCCCCCCCCCCC phosphorylceramide CC(CCOP(O)(═O)OP(O)(═O)O[C@@H]1O[C@H](CO)[C@@H](O[C@ Mannosyl-(N- HMDB @H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@ acetylglucosaminyl) H](O)[C@@H]3O)[C@H](O)[C@H]2NC(C)═O)[C@H](O)[C@H]1NC(C)═ 2- O)CC\C═C(/C)CC\C═C(/C)CC\C═C(/C)CC\C═C(/C)CC\C═C(/C)CC\C═C diphosphodolichol (/C)CC\C═C(/C)CC\C═C(/C)CC\C═C(/C)CC\C═C(/C)CC\C═C(/C)CC\C═C (/C)CC\C═C(/C)CC\C═C(/C)CCC═C(C)C C\C(\C═C\C═C(/C)\C═C\C1═C(C)CCCC1(C)C)═C/C═O Reti-I HMDB C[C@H](N[C@@H](CCC1═CC═CC═C1)C(O)═O)C(═O)N1[C@H]2CCC Ramiprilat HMDB [C@H]2C[C@H]1C(O)═O CC1═C(CC(O)═O)C2═C(C═CC(F)═C2)C1═CC1═CC═C(C═C1)S(C)(═O)═ Sulindac sulfone HMDB O CC1(C)CCSC2═C1C═C(C═C2)C#CC1═NC═C(C═C1)C(O)═O Tazarotenic acid HMDB CC1═C2N═C(OC3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)═O) 12- HMDB C3═C(N═CC═C3)N(C3CC3O)C2═NC═C1 Hydroxynevirapine glucuronide CC1C2CCC(C)(C═C)N2C(═N)NC1═O Are-ine HMDB [H][C@]12OC(O)(C(C)CC1OC)C(═O)C(═O)N1CCCCC1C(═O)OC(C(C)C 31-O- HMDB (O)CC(═O)C(CC═C)\C═C(C)/CC(C)C[C@@H]2OC)C(\C)═C\C1CC[C@ Demethyltacrolimus H](O)C(O)C1 COC1═C(C═C(Cl)C═C1)C(O)═NCCC1═CC═C(C═C1)S(═O)(═O)NC(O)═ 3-cis- HMDB N[C@@H]1CCC[C@H](O)C1 Hydroxycyclohexyl glyburide CN1(═O)CCN(CC1)C(═O)OC1N(C(═O)C2═C1N═CC═N2)C1═NC═C(Cl) nopiclone N-oxide HMDB C═C1 CN1CCN2C(C1)C1═CC═CC═C1CC1═CC(O)═CN═C21 8- HMDB hydroxymirtazapine CC(C)C1═C(\C═C\[C@@H]2C[C@@H](O)CC(═O)O2)C(═NC(═N1)N(C) Rosuvastatin 5 S- HMDB S(C)(═O)═O)C1═CC═C(F)C═C1 lactone NC(CC(O)CNC(N)═N)C(O)═O L-erythro-4- HMDB Hydroxyarginine [H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(═O)OP(O)(═O)OP(O)(O)═ 2-hydroxy-dATP HMDB O)N1C═NC2═C(N)N═C(O)N═C12 CCC1(C)OC(═O)N═C1O 5-ethyl-5-methyl- HMDB 2,4- oxazolidinedione CSCC[C@@H](N)C(O)═O D-Methionine YMDB CCCCC\C═C/C[C@@H](O)\C═C\C═C/C═C/[C@@H](O)CCCC(O)═O Delta(6)- YMDB trans, Delta(8)-cis- leukotriene B4 [H][C@@]1(OC(═O)[C@@H](O)[C@@H]1O)[C@@H](O)CO L-galactono-1,4- YMDB lactone CCCC(C(C)C)C(═O)OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C Valproic acid BMD (O)═O glucuronide [H]C(═O)C(O)C(O)C(OC1OC(CO)C(O)C(OC2OC(CO)C(OC3OC(CO)C Difucosyllacto-N- BMD (O)C(OC4OC(CO)C(OC5OC(C)C(O)C(O)C5O)C(OC5OC(CO)C(O)C(O) hexaose I C5O)C4NC(C)═O)C3O)C(OC3OC(C)C(O)C(O)C3O)C2NC(C)═O)C1O)C (O)CO [H][C@]1(O)O[C@@]([H])(CO)[C@](O)(O[C@@]2([H])O[C@@]([H])(CO) 1,4-beta-D-Glucan BMD [C@](O)(O[C@@]3([H])O[C@@]([H])(CO)[C@]([H])(O)[C@@]([H])(O) [C@]3([H])O)[C@@]([H])(O)[C@]2([H])O)[C@@]([H])(O)[C@]1([H])O [H]C(═O)OCC(COP(O)(═O)OC1[C@@H](O)C(O)C(O)[C@H](O)[C@H]1 1-Phosphatidyl-D- BMD O)OC([H])═O myo-inositol CCCCCC(O)\C═C\C═C/CCCCCCCC(O)═O 13(S)-HODE BMD [H]C(═O)OCC(COP(O)(═O)OC1[C@@H](O)C(O)C(O)[C@H](O)[C@H]1 1-Phosphatidyl-D- BMD O)OC([H])═O myo-inositol [H]\C(\C═C\C(\C)═C\C═C\C═C(/C)\C═C\C═C(/C)\C═C\C1═C(C)C[C@@ (3R,3′R,6′R,9′-cis)- BMD H](O)CC1(C)C)═C(/C)\C═C\[C@@H]1C(C)═C[C@H](O)CC1(C)C b,e-Carotene-3,3′- diol OCC1OC(C(O)C(O)C1O)N1C═NC2═C1N═CN═C2NCC1═CC═CO1 kinetin-9-N- PMN glucoside CCCCCCCCC═CCCCCCCCC(═O)OCC(COP([O−]) 1-18:1-2-18:1-sn- PMN (═O)OCC[N+](C)(C)C)OC(═O)CCCCCCCC═CCCCCCCCC glycerol-3- phosphocholine [N+]C(CO)CC1═CNC═N1 histidinol PMN CC(C)═CCCC(C)═CC═O neral PMN COC1═C(O)C═CC(C═CC(═O)NCCC2═CC═C(O)C═C2)═C1 N-feruloyltyramine PMN CCC═CCC1C(CCCCCCCC([O−])═O)C═CC1═O \12-oxo-cis-10,15- PMN phytodienoate\ [O−]C(═O)CCC1═C2CC3═C(CCC([O−])═O)C(CC([O−])═O)═ uroporphyrinogen- PMN C(CC4═C(CC([O−])═O)C(CCC([O−])═O)═C(CC5═C(CC([O−])═ III O)C(CCC([O−])═O)═C(CC(N2)═C1CC([O−])═O)N5)N4)N3 OC1CC(O)(CC(═O)C1O)C([O−])═O 3-dehydroqui-te PMN CC(C)C(C)C(O)C(O)C(C)C1CCC2C3CC(O)C4CC(O)C(O)CC4(C)C3CC 6alpha-hydroxy- PMN C12C castasterone CC(═O)C═CC1═C(C)CCCC1(C)C beta-ionone PMN CCCCCCCCCCCCCCCC(═O)OC(COC1OC(CO)C(O)C(O)C1O)COC(═ 1-18:2-2-16:0- PMN O)CCCCCCCC═CCC═CCCCCC monogalactosyldiacyl glycerol CC(C)(COP([O−])(═O)OP([O−])(═O)OCC1OC(C(O)C1OP([O−]) 4-coumaryl-CoA PMN ([O−])═O)N1C═NC2═C1N═CN═C2N)C(O)C(═O)NCCC(═O)NCCSC(═O)C═C C1═CC═C(O)C═C1 CC(C)C(═C)CCC(C)C1CC═C2C3═C(CCC12C)C1(C)CCC(O)C(C)C1CC3 \4alpha-methyl- PMN 5alpha-ergosta- 8,14,24(28)-trien- 3beta-ol\ CC(═O)SCCNC(═O)CCNC(═O)C(O)C(C)(C)COP([O−])(═O)OP([O−]) acetyl-CoA PMN (═O)OCC1OC(C(O)C1OP([O−])([O−])═O)N1C═NC2═C1N═CN═C2N CC1(CC2C34OC3CC3C5(C)CCC(OC6OCC(OC7OC(CO)C(O)C(O)C7O) ave-cin A-2 PMN C(O)C6OC6OC(CO)C(O)C(O)C6O)C(C)(CO)C5CCC3(C)C4(C)CC(O)C 2(C)CC1OC(═O)C1═CC═CC═C1)C═O COC1═CC(C═CC(═O)OC(C(O)C(O)C(O)C([O−])═O)C([O−])═ O-si-poylglucarate PMN O)═CC(OC)═C1O OC1C(O)C(OC1COP([O−])([O−])═O)[N+]1═CC(═CC═C1)C([O−])═O beta-nicoti-te D- PMN ribonucleotide CCC═CCC═CC═CC(CCCCCCCC([O−])═O)OO 9(S)-HPOTE PMN COC1═CC(C═CC(═O)SCCNC(═O)CCNC(═O)C(O)C(C)(C)COP([O−]) si-poyl-CoA PMN (═O)OP([O−])(═O)OCC2OC(C(O)C2OP([O−])([O−])═ O)N2C═NC3═C2N═CN═C3N)═CC(OC)═C1O OCC1OC(OC2═C(C═CC([O−])═O)C═CC═C2)C(O)C(O)C1O trans-beta-D- PMN glucosyl-2- hydroxycin-mate OC1C(O)C(O)C(OP([O−])([O−])═O)C(OP([O−])([O−])═O)C1O \D-myo-inositol PMN (1,2)bisphosphate\ CN1CC2═C3OCOC3═CC═C2C2═C1C1═C(C═C2)C═C2OCOC2═C1 dihydrosangui-rine PMN COC1═CC(C═CC(═O)OCC[N+](C)(C)C)═CC(OC)═C1O O-si-poylcholine PMN CC12CCCC(C)(C1C(C═O)C13CC(CCC21)C(═C)C3)C([O−])═O gibberellin A12- PMN aldehyde CC(CCNC1═NC═NC2═C1N═CN2C1OC(CO)C(O)C(O)C1O)COC1OC(C dihydrozeatin-9-N- PMN O)C(O)C(O)C1O glucoside-O- glucoside CSCCCCCCCC(SC1OC(CO)C(O)C(O)C1O)═NO 7- PMN methylthioheptylde sulfoglucosinolate CCCCCCCCCCCCCCCCCCCCCCCCCC(═O)SCCNC(═O)CCNC(═O)C cerotoyl-CoA PMN (O)C(C)(C)COP([O−])(═O)OP([O−])(═O)OCC1OC(C(O)C1OP([O−])([O−])═ O)N1C═NC2═C1N═CN═C2N CC(C)═CC(═O)SCCNC(═O)CCNC(═O)C(O)C(C)(C)COP([O−]) 3-methylcrotonyl- PMN (═O)OP([O−])(═O)OCC1OC(C(O)C1OP([O−])([O−])═ CoA O)N1C═NC2═C1N═CN═C2N COC1═CC(C═CCO)═CC(OC)═C1OC1OC(CO)C(O)C(O)C1O syringin PMN NC1═NC2═C(NC3C(N2)OC(COP([O−])(═O)OP([O−]) molybdopterin PMN (═O)OCC2OC(C(O)C2O)N2C═NC4═C2N═CN═C4N)C([S−])═ adenine C3S)C(═O)N1 dinucleotide COC1═CC═C(C═CC)C═C1 t-anethole PMN [H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H]) CHOLESTERYL Nature [C@@]2([H])CC═C2CC(Cl)CC[C@]12C CHLORIDE CCCC(═O)OC1CC[C@]2(C)C3CC[C@]4(C)[C@H](CCC4C3CC═C2C1) CHOLESTERYL Nature [C@H](C)CCCC(C)C BUTYRATE CCCCC\C═C\C(═O)OCC1═CN═C(C)C(O)═C1COC(═O)\C═C\CCCCC PYRIDOXINE Nature DIOCTENOATE CCCCCCCCCCCCCCCC(═O)OCC1═CN═C(C)C(O)═C1COC(═O)CCCC PYRIDOXINE Nature CCCCCCCCCCC DIPALMITATE CC(═O)OC(C)(C)CCC(═O)C(C)(O)C1C(O)CC2(C)C3CC═C4C(CC(O)C Cucurbitacin B Nature (═O)C4(C)C)C3(C)C(═O)CC12C Cc1sc2nc(nc(N)c2c1C)-c1ccc(C)cc1 5,6-dimethyl-2-(4- Nature methylphenyl)thieno [2,3-d]pyrimidin-4- amine COc1ccccc1C(═O)N1CCC(N)CC1 1-(2- Nature methoxybenzoyl)piperidin- 4-amine hydrochloride Cc1c(F)cccc1NS(═O)(═O)N1CCCC1 N-(3-fluoro-2- Nature methylphenyl)pyrrolidine- 1-sulfo-mide Cc1sc2nc(COC(═O)c3ccc(O)cc3)nc(N)c2c1C {4-amino-5,6- Nature dimethylthieno[2,3- d]pyrimidin-2- yl}methyl 4- hydroxybenzoate CNc1ncnc2sc(C)c(C)c12 N,5,6- Nature trimethylthieno[2,3- d]pyrimidin-4-amine CCCCSc1nc(N)c2c(C)c(C)sc2n1 2-(butylsulfanyl)- Nature 5,6- dimethylthieno[2,3- d]pyrimidin-4-amine CC(C)CNC(═O)C(C)(C)C1═CC═C(C═C1)C1═CC(═CN═C1)C#N 2-(4-(5- Nature cyanopyridin-3- yl)phenyl)-N- isobutyl-2- methylpropamide_8 Cc1sc2nc(CNCc3ccc(Cl)cc3)nc(NCc3ccc(Cl)cc3)c2c1C N-[(4- Nature chlorophenyl)methyl]- 2-({[(4- chlorophenyl)methyl] amino}methyl)- 5,6- dimethylthieno[2,3- d]pyrimidin-4- amine; bis(oxalic acid) COCc1nc2sc(C)c(C)c2c(═O)[nH]1 2-(methoxymethyl)- Nature 5,6-dimethyl- 3H,4H-thieno[2,3- d]pyrimidin-4-one Cc1sc2ncnc(N3CCC(═CC3)c3ccc(O)cc3)c2c1C 4-(1-{5,6- Nature dimethylthieno[2,3- d]pyrimidin-4-yl}- 1,2,3,6- tetrahydropyridin-4- yl)phenol CN(C)c1ccc(CNc2nc(C)nc3sc4CCCc4c23)cc1 N-{[4- Nature (dimethylamino)phenyl] methyl}- 10- methyl-7-thia-9,11- diazatricyclo[6.4.0.0?, ?]dodeca- 1(12),2(6),8,10- tetraen-12-amine CN(C)CCNc1ncnc2sc(C(═O)NCc3ccco3)c(C)c12 4-{[2- Nature (dimethylamino)ethyl] amino}-N-[(furan- 2-yl)methyl]-5- methylthieno[2,3- d]pyrimidine-6- carboxamide Cc1cc2c([nH]c(═S)[nH]c2═O)s1 6-methyl-2- Nature sulfanylidene- 1H,2H,3H,4H- thieno[2,3- d]pyrimidin-4-one COCCN1C(═O)CCc2cc(O)ccc12 6-hydroxy-1-(2- Nature methoxyethyl)- 1,2,3,4- tetrahydroquinolin- 2-one Cc1sc2ncnc(—c3ccc(N)nc3)c2c1C 5-{5,6- Nature dimethylthieno[2,3- d]pyrimidin-4- yl}pyridin-2-amine Cc1sc2nc(CN3CCOCC3)nc(NNC(═O)c3ccccc3)c2c1C N′-{5,6-dimethyl-2- Nature [(morpholin-4- yl)methyl]thieno[2,3- d]pyrimidin-4- yl}benzohydrazide Cc1sc2nc(CNc3cccc(Cl)c3)[nH]c(═O)c2c1C 2-{[(3- Nature chlorophenyl)amino] methyl}-5,6- dimethyl-3H,4H- thieno[2,3- d]pyrimidin-4-one CCn1c(CNc2ncnc3sc(C)c(C)c23)nc2ccccc12 N-[(1-ethyl-1H-1,3- Nature benzodiazol-2- yl)methyl]-5,6- dimethylthieno[2,3- d]pyrimidin-4-amine Cc1sc2nc(nc(NCc3ccc(Cn4cncn4)cc3)c2c1C)-c1cccnc1 5,6-dimethyl-2- Nature (pyridin-3-yl)-N-({4- [(1H-1,2,4-triazol-1- yl)methyl]phenyl}methyl) thieno[2,3- d]pyrimidin-4-amine Cc1sc2ncnc(C1)c2c1C 4-chloro-5,6- Nature dimethylthieno[2,3- d]pyrimidine Cc1ccc(Nc2ncnc3sccc23)cc1 N-(4- Nature methylphenyl)thieno [2,3-d]pyrimidin-4- amine Cc1sc2nc(Cc3ccccc3)[nH]c(═O)c2c1C 2-benzyl-5,6- Nature dimethyl-3H,4H- thieno[2,3- d]pyrimidin-4-one Cc1sc2[nH]c(CN3CCNCC3)nc(═O)c2c1C 5,6-dimethyl-2- Nature [(piperazin-1- yl)methyl]-1H,4H- thieno[2,3- d]pyrimidin-4-one dihydrochloride Cc1sc2nc(nc(N3CCC3)c2c1C)-c1cccnc1 3-[4-(azetidin-1-yl)- Nature 5,6- dimethylthieno[2,3- d]pyrimidin-2- yl]pyridine CC1(C)Cc2c(CO1)sc1n(CC═C)c(═O)nc(N)c21 3-amino-12,12- Nature dimethyl-6-(prop-2- en-1-yl)-11-oxa-8- thia-4,6- diazatricyclo[7.4.0.0?, ?]trideca- 1(9),2(7),3-trien-5- one CCc1c(C)sc2nc(CC)[nH]c(═O)c12 2,5-diethyl-6- Nature methyl-3H,4H- thieno[2,3- d]pyrimidin-4-one Cc1sc2nc(SC(C(N)═O)c3ccccc3)nc(N)c2c1C 2-({4-amino-5,6- Nature dimethylthieno[2,3- d]pyrimidin-2- yl}sulfanyl)-2- phenylacetamide Cc1sc2nc(COC(═O)CSc3ccc(F)cc3)nc(N)c2c1C {4-amino-5,6- Nature dimethylthieno[2,3- d]pyrimidin-2- yl}methyl 2-[(4- fluorophenyl)sulfanyl] acetate CC1CCN(Cc2nc(NCc3ccccc3CO)c3c(C)c(C)sc3n2)CC1 {2-[({5,6-dimethyl- Nature 2-[(4- methylpiperidin-1- yl)methyl]thieno[2,3- d]pyrimidin-4- yl}amino)methyl]phenyl} methanol C1c1ccc(cc1)C(═O)Nc1ncnc2sc3CCCCc3c12 4-chloro-N-{8-thia- Nature 4,6- diazatricyclo[7.4.0.0?, ?]trideca- 1(9),2,4,6-tetraen- 3-yl}benzamide COc1ccc(Nc2nc(C)nc3sc4CCCc4c23)cc1OC N-(3,4- Nature dimethoxyphenyl)- 10-methyl-7-thia- 9,11- diazatricyclo[6.4.0.0?, ?]dodeca- 1(12),2(6),8,10- tetraen-12-amine CCc1cc2c(Nc3ccncc3)ncnc2s1 N-{6- Nature ethylthieno[2,3- d]pyrimidin-4- yl}pyridin-4-amine Nc1nc(O)nc2sc3CCCCc3c12 3-amino-8-thia-4,6- Nature diazatricyclo[7.4.0.0?, ?]trideca- 1(9),2,4,6-tetraen- 5-ol NNc1nc(N)nc2sc3CCCCc3c12 3-hydrazinyl-8-thia- Nature 4,6- diazatricyclo[7.4.0.0?, ?]trideca- 1(9),2,4,6-tetraen- 5-amine CCC(C)Cc1c(C)sc2nc(CNc3ccccc3)[nH]c(═O)c12 6-methyl-5-(2- Nature methylbutyl)-2- [(phenylamino)methyl]- 3H,4H- thieno[2,3- d]pyrimidin-4-one CN(CCC(O)c1ccccc1)c1ncnc2sc(C(O)═O)c(C)c12 4-[(3-hydroxy-3- Nature phenylpropyl)(methyl) amino]-5- methylthieno[2,3- d]pyrimidine-6- carboxylic acid CN(Cc1ccc(Cl)cc1)c1ncnc2sc3CCCCCc3c12 N-[(4- Nature chlorophenyl)methyl]- N-methyl-8-thia- 4,6- diazatricyclo[7.5.0.0?, ?]tetradeca- 1(9),2,4,6-tetraen- 3-amine Cc1c(sc2ncnc(NCC3CCCO3)c12)C(═O)NCCC1═CCCCC1 N-[2-(cyclohex-1- Nature en-1-yl)ethyl]-5- methyl-4-{[(oxolan- 2- yl)methyl]amino}thieno [2,3- d]pyrimidine-6- carboxamide Nc1ncnc2sc3CNCCc3c12 8-thia-4,6,11- Nature triazatricyclo[7.4.0. 0?,?]trideca- 1(9),2,4,6-tetraen- 3-amine hydrochloride CC1CCN(CC1)c1nc(CN2CCCC2)nc2sc(C)c(C)c12 1-{5,6-dimethyl-2- Nature [(pyrrolidin-1- yl)methyl]thieno[2,3- d]pyrimidin-4-yl}-4- methylpiperidine CN1CCN(CC1)c1ncnc2sc(C(═O)NCC═C)c(C)c12 5-methyl-4-(4- Nature methylpiperazin-1- yl)-N-(prop-2-en-1- yl)thieno[2,3- d]pyrimidine-6- carboxamide COCCCNc1ncnc2sc(C(═O)NCCN3CCCC3)c(C)c12 4-[(3- Nature methoxypropyl)amino]- 5-methyl-N-[2- (pyrrolidin-1- yl)ethyl]thieno[2,3- d]pyrimidine-6- carboxamide CCn1cnnc1CNc1ncnc2sc3CCCCCc3c12 N-[(4-ethyl-4H- Nature 1,2,4-triazol-3- yl)methyl]-8-thia- 4,6- diazatricyclo[7.5.0. 0?,?]tetradeca- 1(9),2,4,6-tetraen- 3-amine Cc1sc2ncnc(N3CCCC(C3)C(═O)NCC3CC3)c2c1C N- Nature (cyclopropylmethyl)- 1-{5,6- dimethylthieno[2,3- d]pyrimidin-4- yl}piperidine-3- carboxamide Cc1sc2[nH]c(CCC(O)═O)nc(═O)c2c1C 3-{5,6-dimethyl-4- Nature oxo-1H,4H- thieno[2,3- d]pyrimidin-2- yl}propanoic acid [O−][N+](═O)c1cccc(c1)C(═O)Nc1ncnc2sc3CCCc3c12 3-nitro-N-{7-thia- Nature 9,11- diazatricyclo[6.4.0. 0?,?]dodeca- 1(12),2(6),8,10- tetraen-12- yl}benzamide Cc1c(sc2ncnc(NCCCN3CCCC3═O)c12)C(═O)NCCc1ccccc1 5-methyl-4-{[3-(2- Nature oxopyrrolidin-1- yl)propyl]amino}-N- (2- phenylethyl)thieno [2,3-d]pyrimidine-6- carboxamide Cc1cc2c(N)nc(═O)n(CC(═O)NCc3ccccc3)c2s1 2-{4-amino-6- Nature methyl-2-oxo- 1H,2H-thieno[2,3- d]pyrimidin-1-yl}-N- benzylacetamide Clc1ccc(cc1)C(═O)Nc1ncnc2sc3CCCc3c12 4-chloro-N-{7-thia- Nature 9,11- diazatricyclo[6.4.0. 0?,?]dodeca- 1(12),2(6),8,10- tetraen-12- yl}benzamide Cc1nnc(NC(═O)C2CCN(CC2)c2ncnc3sc(C)c(C)c23)o1 1-{5,6- Nature dimethylthieno[2,3- d]pyrimidin-4-yl}-N- (5-methyl-1,3,4- oxadiazol-2- yl)piperidine-4- carboxamide C(C1CCN(CC1)c1ncnc2sc3CCCc3c12)c1ccccc1 12-(4- Nature benzylpiperidin-1- yl)-7-thia-9,11- diazatricyclo[6.4.0. 0?,?]dodeca- 1(12),2(6),8,10- tetraene CCn1cnnc1CNc1nc(CN2CCCC2)nc2sc(C)c(C)c12 N-[(4-ethyl-4H- Nature 1,2,4-triazol-3- yl)methyl]-5,6- dimethyl-2- [(pyrrolidin-1- yl)methyl]thieno[2,3- d]pyrimidin-4- amine CCc1cccc(NC(C)c2nc3sc(C)c(C)c3c(═O)[nH]2)c1 2-{1-[(3- Nature ethylphenyl)amino] ethyl}-5,6-dimethyl- 3H,4H-thieno[2,3- d]pyrimidin-4-one C(Nc1ncnc2sc3CCCCc3c12)C1COc2ccccc2C1 N-[(3,4-dihydro-2H- Nature 1-benzopyran-3- yl)methyl]-8-thia- 4,6- diazatricyclo[7.4.0. 0?,?]trideca- 1(9),2,4,6-tetraen- 3-amine NC(═O)CCOc1ccccc1NS(N)(═O)═O 3-[2- Nature (sulfamoylamino)phenoxy] propa-mide COc1c(C)ccc(NS(N)(═O)═O)c1C N-(3-methoxy-2,4- Nature dimethylphenyl)amino sulfo-mide CCN1[C@H]([C@@H](CC1═O)C(O)═O)c1ccc(OC)cc1OC (2R,3R)-2-(2,4- Nature dimethoxyphenyl)- 1-ethyl-5- oxopyrrolidine-3- carboxylic acid COc1cc(F)c(F)cc1C(═O)C1CCN(CC1)C(C)═O 1-[4-(4,5-difluoro-2- Nature methoxybenzoyl)piperidin- 1-yl]ethan- 1-one NC(═N)c1cc(F)ccc1NS(N)(═O)═O 5-fluoro-2- Nature (sulfamoylamino)benzene- 1- carboximidamide Cc1ccc(NCc2cccc3cccnc23)cc1NS(C)(═O)═O N-(2-methyl-5- Nature {[(quinolin-8- yl)methyl]amino}phenyl) methanesulfo- mide FC(F)(F)c1ccc(CCNc2ncnc3sc4CCCc4c23)cc1 N-{2-[4- Nature (trifluoromethyl)phenyl] ethyl}-7-thia- 9,11- diazatricyclo[6.4.0. 0?,?]dodeca- 1(12),2(6),8,10- tetraen-12-amine CC(═O)N1CCC(CC1)NCc1ccc2OCCc2c1 1-(4-{[(2,3-dihydro- Nature 1-benzofuran-5- yl)methyl]amino}piperidin- 1-yl)ethan-1- one CN(C)CCNc1ncnc2sc(C(═O)N(C)C)c(C)c12 4-{[2- Nature (dimethylamino)ethyl] amino}- N,N,5- trimethylthieno[2,3- d]pyrimidine-6- carboxamide CC(═O)Nc1ccc(N\C(═N/S(═O)(═O)c2ccccc2)c2ccccc2)cc1 N-{4-[(Z)-N′- Nature (benzenesulfonyl)benzene imidamido]phenyl} acetamide Cc1ccc(N\C(═N/S(═O)(═O)c2ccc(Cl)cc2)c2ccc(C)cc2)cc1 (Z)-N′-(4- Nature chlorobenzenesulfonyl)- 4-methyl-N-(4- methylphenyl)benzene- 1- carboximidamide NS(═O)(═O)Nc1ccccc1C(═O)NC1CC1 N-cyclopropyl-2- Nature (sulfamoylamino)benzamide CCC(Cl)C(═O)N1CCc2c1cccc2OC 2-chloro-1-(4- Nature methoxy-2,3- dihydro-1H-indol-1- yl)butan-1-one CC(C)CN1C(═O)CCc2cc(O)ccc12 6-hydroxy-1-(2- Nature methylpropyl)- 1,2,3,4- tetrahydroquinolin- 2-one COc1cccc2N(CCc12)C(═O)CN═[N+]═[N−] 2-azido-1-(4- Nature ethoxy-2,3- dihydro-1H-indol-1- yl)ethan-1-one O═S(═O)(NCc1ccccc1)Nc1ccccc1OCc1ccccn1 N-benzyl({2- Nature [(pyridin-2- yl)methoxy]phenyl} amino)sulfo-mide Cc1sc2nc(Cc3ccc(cc3)[N+]([O−])═O)[nH]c(═O)c2c1C 5,6-dimethyl-2-[(4- Nature nitrophenyl)methyl]- 3H,4H-thieno[2,3- d]pyrimidin-4-one Cc1ccccc1N\C(═N/S(═O)(═O)c1ccc(Cl)cc1)c1ccccc1 (Z)-N′-(4- Nature chlorobenzenesulfonyl)- N-(2- methylphenyl)benzene carboximidamide CN(C)S(═O)(═O)Nc1cc(ccc1C)C(F)(F)F dimethyl({[2- Nature methyl-5- (trifluoromethyl)phenyl] sulfamoyl})amine O═S(═O)(Nc1nccs1)c1ccc(N\C(═N/S(═O)(═O)c2ccccc2)c2ccccc2)cc1 (Z)-N′- Nature (benzenesulfonyl)- N-{4-[(1,3-thiazol-2- yl)sulfamoyl]phenyl} benzenecarboximidamide CN(C)Cc1nc2sc(C)c(C)c2c(═O)[nH]1 2- Nature [(dimethylamino)methyl]- 5,6-dimethyl- 3H,4H-thieno[2,3- d]pyrimidin-4-one CC(═O)N1CCC(CC1)C(═O)c1ccc2OCCc2c1 1-[4-(2,3-dihydro-1- Nature benzofuran-5- carbonyl)piperidin- 1-yl]ethan-1-one CC1CCCC(C)N1C1═NS(═O)(═O)c2cc(ccc12)[N+]([O−])═O 3-(2,6- Nature dimethylpiperidin-1- yl)-6-nitro-1??,2- benzothiazole-1,1- dione COc1ccccc1CC(═O)N1CCC2(CC1)NN(C(═O)N2)c1cccc(F)c1 2-(3-fluorophenyl)- Nature 8-[2-(2- methoxyphenyl)acetyl]- 1,2,4,8- tetraazaspiro[4.5]decan- 3-one CNC(═O)c1ccc(NC(═O)NC2CCOc3ccccc23)c(C)c1 4-{[(3,4-dihydro-2H- Nature 1-benzopyran-4- yl)carbamoyl]amino}- N,3- dimethylbenzamide CCOc1cc2CC(C)Oc2cc1NS(N)(═O)═O N-(5-ethoxy-2- Nature methyl-2,3-dihydro- 1-benzofuran-6- yl)aminosulfo-mide CC(═O)N1CCC2C(C1)Oc1ccc(N)cc21 1-{12-amino-8-oxa- Nature 5- azatricyclo[7.4.0.0?, ?]trideca- 1(13),9,11-trien-5- yl}ethan-1-one COc1ccc(Nc2nc(Cc3ccccc3)nc3sc4CCCCc4c23)c(OC)c1 5-benzyl-N-(2,4- Nature dimethoxyphenyl)- 8-thia-4,6- diazatricyclo[7.4.0.0?, ?]trideca- 1(9),2,4,6-tetraen- 3-amine CCCCNC(═O)c1sc2nc(C)nc(N3CCCC3)c2c1C N-butyl-2,5- Nature dimethyl-4- (pyrrolidin-1- yl)thieno[2,3- d]pyrimidine-6- carboxamide COc1ccc(CN2CC(CCC2═O)C(O)═O)c(OC)c1 1-[(2,4- Nature dimethoxyphenyl)methyl]- 6- oxopiperidine-3- carboxylic acid CC(C)Oc1ccc(NS(N)(═O)═O)c(C)c1 N-[2-methyl-4- Nature (propan-2- yloxy)phenyl]amino sulfo-mide O═Cc1ccccc1OCC(═O)N1CCCCC1 2-[2-oxo-2- Nature (piperidin-1- yl)ethoxy]benzaldehyde CC(C)(C)C1CCc2c(C1)sc1[nH]c(═S)[nH]c(═S)c21 11-tert-butyl-8-thia- Nature 4,6- diazatricyclo[7.4.0.0?, ?]trideca- 1(9),2(7)-diene-3,5- dithione COc1ccccc1CN1CCC(═O)CC1═O 1-[(2- Nature methoxyphenyl)methyl] piperidine-2,4- dione COC(═O)Cc1nc(N2CCN(CC2)c2ccccc2)c2c(C)c(C)sc2n1 methyl 2-[5,6- Nature dimethyl-4-(4- phenylpiperazin-1- yl)thieno[2,3- d]pyrimidin-2- yl]acetate CCN(CC)Cc1nc(N2CCN(Cc3nc4ccccc4c(═O)[nH]3)CC2)c2c(C)c(C)sc2n1 2-[(4-{2- Nature [(diethylamino)methyl]- 5,6- dimethylthieno[2,3- d]pyrimidin-4- yl}piperazin-1- yl)methyl]-3,4- dihydroqui-zolin-4- one CCCn1c(SCc2nc(N)c3c(C)c(C)sc3n2)n[nH]c1═O 3-[({4-amino-5,6- Nature dimethylthieno[2,3- d]pyrimidin-2- yl}methyl)sulfanyl]- 4-propyl-4,5- dihydro-1H-1,2,4- triazol-5-one Cc1sc2ncnc(NCC3CCCN(C3)S(C)(═O)═O)c2c1C N-[(1- Nature methanesulfonylpiperidin- 3-yl)methyl]- 5,6- dimethylthieno[2,3- d]pyrimidin-4-amine COc1ccccc1CCC(═O)NC1CCN(CC1)c1cc(nc(C)n1)C(F)(F)F 3-(2- Nature methoxyphenyl)-N- {1-[2-methyl-6- (trifluoromethyl)pyrimidin- 4-yl]piperidin- 4-yl}propa-mide CC(C)c1cc(Cl)ccc1OCC1CCNCC1 4-{[4-chloro-2- Nature (propan-2- yl)phenoxy]methyl} piperidine hydrochloride Cc1c(sc2nc[nH]c(═O)c12)C(═O)Nc1cccc(C)c1 5-methyl-N-(3- Nature methylphenyl)-4- oxo-3H,4H- thieno[2,3- d]pyrimidine-6- carboxamide COc1ccc(\C═N\Nc2nc3sc(C)c(C)c3c(═O)[nH]2)cc1 2-[(E)-2-[(4- Nature methoxyphenyl)methylidene] hydrazin- 1-yl]-5,6-dimethyl- 3H,4H-thieno[2,3- d]pyrimidin-4-one CCOc1ccccc1C(CC(O)═O)NC(C)═O 3-acetamido-3-(2- Nature ethoxyphenyl)propanoic acid CC(C)CCOc1ccccc1C(═O)Nc1ccc(N)cc1C N-(4-amino-2- Nature methylphenyl)-2-(3- methylbutoxy)benzamide CCc1ccc(OCC(═O)NC2CCN(CC2)C(C)c2ccccc2)cc1 2-(4-ethylphenoxy)- Nature N-[1-(1- phenylethyl)piperidin- 4-yl]acetamide C(N1CCN(CC1)c1ncnc2sc3CCCc3c12)c1ccccc1 12-(4- Nature benzylpiperazin-1- yl)-7-thia-9,11- diazatricyclo[6.4.0.0?, ?]dodeca- 1(12),2(6),8,10- tetraene Cn1/c(═N/C(═O)[C@@]([C@](F)(F)F)([C@](F)(F)F)Br)cc([O−])n(c1═O)C Nature Cn1/c(═N/C(═O)[C@]([C@](F)(F)F)([C@](F)(F)F)Cl)cc([O−])n(c1═O)C Nature CC[C@@]1(C(═N)N(C(═O)N(C1═O)C)C)CC Nature CC[C@@]1(C(═N)N(C(═O)N(C1═O)C)CC)CC Nature CCC[C@]1(C(═N)N(C(═O)N(C1═O)C)C)CCC Nature CCCN1C(═N)[C@](C(═O)N(C1═O)C)(CC)CC Nature CC[C@@]1(/C(═N/[C@@H](C)C)NC(═O)N(C1═O)C)CC Nature CCC[C@]1(C(═N)NC(═O)N(C1═O)C)CCC Nature CCCC[C@@]1(C(═N)N(C(═O)N(C1═O)C)C)CCCC Nature C[C@@H](C)CC[C@@]1(C(═[NH+])NC(═S)N═C1[O−])CC[C@H](C)C Nature CCC/N═C/1[C@](C(═O)N(C(═O)N1)C)(CC)CC Nature CCC[C@]1(/C(═N/C)NC(═O)N(C1═O)C)CCC Nature CCC[C@]1(C(═[NH+])NC(═S)N═C1[O−])CCC Nature CCCC/N═C/1[C@](C(═O)N(C(═O)N1)C)(CC)CC Nature CCCC[C@@]1(C(═N)NC(═O)N(C1═O)C)CCCC Nature CCCC[C@@]1(/C(═N/C)NC(═O)N(C1═O)C)CCCC Nature CCN(CC)/C(═N\[S@](═O)(═O)c1ccc(cc1)C)/C(═C\1N(/C(═[N+]/[C@](C) Nature (C)C)S1)C)C c1cn(c(═O)nc1N)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[P@](═O)([O−]) Nature O[P@@](═O)([O−])[O−])O)O CC[C@@]1(C(═NC(═O)N(C1═O)C)Nc1ccc(cc1)Cl)CC Nature CC[C@@]1(/C(═N/c2ccccc2)N(C(═O)N(C1═O)C)C)CC Nature c1cn(c(═O)nc1N)[C@H]1C[C@@H]([C@H](O1)CO[P@](═O)([O−]) Nature O[P@@](═O)([O−])[O−])O CC[C@@]1(C(═N)NC(═O)N(C1═O)C)c1ccccc1 Nature CC[C@]1(C(═N)NC(═O)N(C1═O)C)c1ccccc1 Nature c1cn(c(═O)nc1N)[C@@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O Nature c1cn(c(═O)nc1N)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O Nature c1cn(c(═O)nc1N)[C@H]1[C@H]([C@@H]([C@H](O1)CO)O)O Nature c1[n+]c(nc(═O)n1[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)N Nature c1cn(c(═O)nc1N)[C@@H]1[C@H]([C@@H]([C@H](O1)CO)O)O Nature CC[C@@]1(/C(═N/Cc2ccc(cc2)OC)NC(═O)N(C1═O)C)CC Nature c1cn(c(═O)nc1N)[C@H]1[C@@H]([C@@H]([C@H](O)CO[P@](═O)([O−]) Nature [O−])O)O CC(═O)c1c(nc2n(c1═O)CCC2)N Nature CC[C@@]1(C(═NC(═O)NC1═O)Nc1cccc(c1)C)CC Nature CC[C@@]1(C(═NC(═O)NC1═O)Nc1ccccc1OC)CC Nature c1cn(c(═O)nc1N)[C@H]1C[C@@H]([C@H](O1)CO[P@](═O)([O−])[O−])O Nature CC/C(═N\c1cc([n+]c2c1cccc2)N(C)C)N(C)C Nature CCC[C@]1(C(═NC(═O)NC1═O)Nc1cccc(c1)C)CCC Nature c1cn(c(═O)nc1N)[C@@H]1C[C@H]([C@@H](O1)CO)O Nature c1cn(c(═O)nc1N)[C@@H]1C[C@@H]([C@@H](O1)CO)O Nature c1cn(c(═O)nc1N)[C@H]1C[C@@H]([C@@H](O1)CO)O Nature c1cn(c(═O)nc1N)[C@H]1C[C@H]([C@@H](O1)CO)O Nature c1cn(c(═O)nc1N)[C@H]1C[C@@H]([C@H](O1)CO)O Nature CCC[C@]1(C(═NC(═O)NC1═O)Nc1ccc(cc1)OC)CCC Nature C/N═C1\C/C(═[N+]/C)N([C@H](c2c1cccc2)O)C Nature C/N═C1\C/C(═[N+]/C)N([C@@H](c2c1cccc2)O)C Nature CCC[C@]1(C(═[N+]C(═O)NC1═O)N)CCC Nature CCC[C@]1(C(═NC(═O)NC1═O)Nc1ccccc1)CCC Nature CCCC[C@@]1(C(═NC(═O)NC1═O)Nc1ccccc1)CCCC Nature Cc1cc(c(cc1)/N═C/[N+](═C/Nc1c(cc(cc1)C)C)C)C Nature CN(C)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CCCC[C@@]1(C(═[N+]C(═O)NC1═O)N)CCCC Nature c1cn(c(═O)nc1N)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[P@](═O)([O−])O[P@](═O)([O−]) Nature O[P@](═O)([O−])[O−])O)O c1cn(c(═O)nc1N)[C@H]1C[C@@H]([C@H](O1)CO[P@](═O)([O−])O[P@](═O)([O−]) Nature O[P@](═O)([O−])[O−])O C[N@@+](C)(C)CCO[P@](═O)([O−])O[P@@](═O)([O−]) Nature OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1ccc(nc1═O)N)O)O CC[C@@H](C)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CC[C@H](C)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature C[C@H](C)CNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)N(CCO)CCO Nature C[C@@H](C)CCCNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CCCCCC[C@@H](C)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CCCCCC[C@H](C)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CCCCN(CCCC)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CC(═O)NCCCCNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CCC(═O)NCCCCCNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature C/C(═N\c1c2ccccc2[n+]c2c1CCN2C)N(C)C Nature CC(═O)N(c1ccc(cc1)OC)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CN(CC[C@H](CC(═O)N[C@H]1C═C[C@@H](O[C@@H]1C(═O)[O−]) Nature n1ccc(nc1═O)N)[NH3+])C(═[NH2+])N CN(CC[C@@H](CC(═O)N[C@H]1C═C[C@@H](O[C@@H]1C(═O)[O−]) Nature n1ccc(nc1═O)N)[NH3+])C(═[NH2+])N CN(CC[C@@H](CC(═O)N[C@@H]1C═C[C@@H](O[C@@H]1C(═O)[O−]) Nature n1ccc(nc1═O)N)[NH3+])C(═[NH2+])N CN(CC[C@H](CC(═O)N[C@@H]1C═C[C@@H](O[C@@H]1C(═O)[O−]) Nature n1ccc(nc1═O)N)[NH3+])C(═[NH2+])N CNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1cc(cc(c1OC)OC)CNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)NCCCO Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)NCCCC[NH3+] Nature COCCCNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CCOCCCNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CCCCCCCNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)NCCCCCC[NH3+] Nature C[C@@H]1C[C@H](CN(C1)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC)C Nature C[C@H]1C[C@@H](CN(C1)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC)C Nature Cc1cc(cc(c1)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC)C Nature Cc1ccc(c(c1)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC)C Nature C[C@H](C)c1ccc(cc1)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature C[C@H](C)c1ccccc1Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature Cc1cc(ccc1Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC)OC Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)Nc1ccc(cc1)C(═O)[O−] Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)Nc1ccc(cc1)C(═O)OC Nature CCOC(═O)[C@@H]1CCN(CC1)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1cc(cc(c1)OC)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CCOC(═O)[C@H]1CCCN(C1)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CCOC(═O)[C@@H]1CCCN(C1)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1ccc(c(c1)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC)OC Nature CCC(═O)NCCCCCCNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CCOC(═O)c1ccc(cc1)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1ccc(cc1OC)CCNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CCCCOC(═O)c1ccc(cc1)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CN(C)/C(═N\c1cc[n+]cc1)c1ccccc1 Nature CN(C)c1cc(c2ccccc2n1)/N═C(\c1ccccc1)N(C)C Nature CN(C)c1cc(c2ccccc2[n+]1)/N═C(/Cc1ccccc1)N(C)C Nature Cc1cc(c2ccccc2[n+]1)/N═C(\c1ccccc1)N(C)C Nature C[C@H]1CCCN(C1)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature C[C@@H]1CCCN(C1)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)Nc1ccccc1Br Nature C[C@@H](c1ccccc1)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature C[C@H](c1ccccc1)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1ccc(cc1)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1cccc(c1)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CCOc1ccccc1Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1ccc(cc1)CNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature C[C@@H](CCc1ccccc1)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature C[C@H](CCc1ccccc1)Nc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1ccc(cc1)CCNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)Nc1cc(c(cc1C(═O)OC)OC)OC Nature C[C@]1(Cc2c(cc3c(n2)n(cnc3═O)Cc2ccccc2)CO1)C Nature CC(═O)N(c1ccc2c(c1)OCCO2)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)NCc1ccccc1 Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)NCCc1ccccc1 Nature C[C@H]1Cc2ccccc2N1c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature C[C@@H]1Cc2ccccc2N1c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature COc1cc2c(cc1OC)c1cc3nc4ccccc4c(═O)n3c(═O)n1CC2 Nature Cc1ccc(cc1)[C@@H](CCN(c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC)C(═O)C)c1ccco1 Nature Cc1ccc(cc1)[C@H](CCN(c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC)C(═O)C)c1ccco1 Nature Cc1ccc(cc1)NC(═O)C1═C(CCC1)/[N+]═C\1CCCN1C Nature CC[C@@H](C)[C@@]1(C(═N)N(C(═NC1═O)[O−])C)CC Nature CC[C@H](C)[C@@]1(C(═N)N(C(═NC1═O)[O−])C)CC Nature CC[C@@]1(C(═N)N(C(═NC1═O)[O−])C)CC Nature C[C@@H](C)C[C@]1(C(═N)NC(═NC1═O)[O−])C[C@@H](C)C Nature CC(═O)N(CC[C@@H](c1ccccc1)c1ccco1)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CC(═O)N(CC[C@H](c1ccccc1)c1ccco1)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CCC[C@@]1(C(═N)N(C(═NC1═O)[O−])C)CC Nature CCC[C@]1(C(═N)N(C(═NC1═O)[O−])C)CC Nature C[C@@H](C)CC[C@@]1(C(═N)N(C(═NC1═O)[O−])C)CC[C@H](C)C Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)NCc1ccc2c(c1)OCO2 Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)N1CCc2ccccc2C1 Nature CCC[C@]1(C(═N)N(C(═NC1═O)[O−])C)CCC Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)n1ccc2c1cccc2 Nature Cc1ccc(c(c1C#N)/N═C(\C)N(C)C)C Nature CCCCN1C(═N)[C@](C(═NC1═O)[O−])(CC)CC Nature CCCCC[C@@]1(C(═N)N(C(═NC1═O)[O−])C)CC Nature CCCCC[C@]1(C(═N)N(C(═NC1═O)[O−])C)CC Nature c1ccc2c(c1)c1c(c(═O)o2)[C@H](C2═C(O1)NC═N[C@H]2N)c1ccc(cc1)Br Nature c1ccc2c(c1)c1c(c(═O)o2)[C@@H](C2═C(O1)NC═N[C@H]2N)c1ccc(cc1)Br Nature c1ccc2c(c1)c1c(c(═O)o2)[C@H](C2═C(O1)NC═N[C@@H]2N)c1ccc(cc1)Br Nature c1ccc2c(c1)c1c(c(═O)o2)[C@@H](C2═C(O1)NC═N[C@@H]2N)c1ccc(cc1)Br Nature CCCC[C@@]1(C(═N)N(C(═NC1═O)[O−])C)CCCC Nature C/C(═N\c1ccc(cc1C#N)Cl)N(C)C Nature Cc1ccc(c(c1)C#N)/N═C(\C)N(C)C Nature C/C(═N\c1ccccc1C#N)N(C)C Nature COc1ccccc1[C@@H](CCNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC)c1ccco1 Nature COc1ccccc1[C@H](CCNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC)c1ccco1 Nature CCCCCC[C@@]1(C(═N)NC(═NC1═O)[O−])CCCCCC Nature CC[C@@]1(/C(═N/CCc2ccc(c(c2)OC)OC)NC(═NC1═O)[O−])CC Nature CC[C@@]1(/C(═N/[C@@H](C)c2ccccc2)NC(═NC1═O)[O−])CC Nature CC[C@@]1(/C(═N/[C@H](C)c2ccccc2)NC(═NC1═O)[O−])CC Nature CC[C@@]1(/C(═N/Cc2ccc(cc2)OC)NC(═NC1═O)[O−])CC Nature CC[C@@]1(/C(═N/[C@@H](C)Cc2ccccc2)NC(═NC1═O)[O−])CC Nature CC[C@@]1(/C(═N/[C@H](C)Cc2ccccc2)NC(═NC1═O)[O−])CC Nature Cc1ccc(cc1)/C═C/1C(═NC(═O)N═C1[NH−])N Nature CC[C@@]1(/C(═N/Cc2ccccc2)NC(═NC1═O)[O−])CC Nature Cc1ccc(c(c1C#N)/N═C/1CCCCCN1C)C Nature CC[C@@]1(/C(═N/CCc2ccccc2)NC(═NC1═O)[O−])CC Nature c1ccc2c(c1)CN1Cc3ccccc3C1═[N+]C2═N Nature CN1CCCC\1═N/c1ccc(cc1C#N)Cl Nature CN1CCCCC\1═N/c1ccc(cc1C#N)Br Nature CN1CCCCC\1═N/c1ccc(cc1C#N)Cl Nature CN1CCCCCC\1═N/c1ccc(cc1C#N)Cl Nature CN(C)/C(═N/c1ccccc1C#N)c1ccccc1 Nature Cc1cc(c(c(c1)C#N)/N═C/1CCCN1Cc1ccccc1)C Nature Cc1ccc(c(c1C#N)/N═C/1CCCN1Cc1ccccc1)C Nature CN1C2═NNC═[N+][C@@]2(C(═O)N(C1═O)C)[O−] Nature c1cnccc1c1ccn2c(c1)ncc1sc(═O)nc21 Nature C[C@@]1([C@@H](O[C@]([C@@]([C@]1(C)C)(C)C)(C)C)N1[C@@H]2C(═C(N1)Br)C(═O)N Nature C═N2)C C[C@]1([C@H](O[C@@]([C@]([C@@]1(C)C)(C)C)(C)C)N1[C@@H]2C(═C(N1)Br)C(═O)NC═ Nature N2)C Cc1cc2c(cc1/N═C/N(C)C)nc1c(n2)c(═O)n(c(═O)n1C)C Nature C[NH+](C)CCNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CC[NH+](CC)CCNc1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CC[NH+]1CCN(CC1)c1cc2n(c(═O)n1)CCc1c2cc(c(c1)OC)OC Nature CN1C2═NNC═N[C@]2(C(═O)N(C1═O)C)O Nature c1c2c([nH]n1)nc[nH]c2═O Nature COc1cc2c(cc1OC)c1cc(nc(═O)n1CC2)N1CC[NH2+]CC1 Nature CC(═O)OC[C@H]1[C@H]([C@@](CO1)(N1C═N[C@@H]2[C@@H]1N═CNC2═O)OC(═O)C)O Nature C(═O)C CC(═O)OC[C@@H]1[C@H]([C@@](CO1)(N1C═N[C@@H]2[C@@H]1N═CNC2═O)OC(═O)C) Nature OC(═O)C CC(═O)OC[C@@H]1[C@@H]([C@@](CO1)(N1C═N[C@@H]2[C@@H]1N═CNC2═O)OC(═O) Nature C)OC(═O)C CC(═O)OC[C@H]1[C@@H]([C@@](CO1)(N1C═N[C@@H]2[C@@H]1N═CNC2═O)OC(═O)C) Nature OC(═O)C C[C@H](C)[C@@]1(C(═O)N═C(N1)c1ccccc1[N+](═O)[O−])C Nature C[C@H](C)[C@]1(C(═O)N═C(N1)c1ccccc1[N+](═O)[O−])C Nature c1cc2cccc3c2c(c1)C(═N3)N1C[C@@H]2C[C@H](C1)c1cccc(═O)n1C2 Nature c1ccc(cc1)Cc1nc2ccccc2c(═O)n1NC(═O)c1c(═O)c2cccc3c2n(c1[O−])CC3 Nature CCNC(═O)[C@]12C(═NN═C[N−]1)N(C(═O)N2C)C Nature CCNC(═O)[C@@]12C(═NN═C[N−]1)N(C(═O)N2C)C Nature CCCNC(═O)[C@]12C(═NN═C[N−]1)N(C(═O)N2C)C Nature CCCNC(═O)[C@@]12C(═NN═C[N−]1)N(C(═O)N2C)C Nature CCOC(═O)/C(═N/Nc1ccc(cc1)C)n1c(cc(nn(c1═S)C)C)[S−] Nature CCCCNC(═O)[C@]12C(═NN═C[N−]1)N(C(═O)N2C)C Nature CCCCNC(═O)[C@@]12C(═NN═C[N−]1)N(C(═O)N2C)C Nature CCOC(═O)/C(═N/Nc1ccccc1)n1c(cc(nn(c1═S)C)C)[S−] Nature c1c(nc(═O)n(n1)[C@H]1[C@@H]([C@@H]([C@@H](O1)CO)O)O)NCC(═O)N Nature CCOC(═O)c1nn(c2cc(nn(c(═S)n12)C)C)c1ccc(cc1)C Nature CCC[C@@]1(/C(═N/c2cccnc2)NC(═NC1═O)[O−])CCC Nature C[N+]1═C2C(═[N+]C(═N)N═C2[O−]) Nature NC[C@@H]1CNc1ccc(cc1)C(═O)N[C@@H](CCC(═O)O)C(═O)[O−] Cc1c(nc(═O)n(n1)[C@@H]1CCCO1)N Nature CCOC(═O)c1nn(c2cc(nn(c(═S)n12)C)C)c1ccccc1 Nature c1ccc(cc1)C(═O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1c(═O)nc(cn1)NCC(═O)N)O)O Nature c1c(nc(═O)n(n1)[C@H]1CCCO1)N Nature c1c(nc(═O)n(n1)[C@@H]1CCCO1)N Nature C[C@]1(C(═[N+]([O−])C(═N1)c1cccnc1)c1ccccc1)C Nature c1cc(ccc1C(═O)N[C@@H](CCC(═O)O)C(═O)[O−])NC[C@@H]1CNC2═[N+]C(═N)N═C([O−]) Nature C2═[N+]1C═O c1cc2cccc3c2c(c1)/c(═N/C(═O)c1ccc(cc1[N+](═O)[O−])[N+](═O)[O−])[nH]3 Nature c1c2c(ncn2)[nH]c(═O)[nH]1 Nature c1ccc(cc1)/C(═N/OCO/N═C(/C1═CC═CCC1)N)N Nature c1ccc(cc1)C1═NN2CNC(═N)[N+]═C2CC1 Nature Cc1cc(no1)/[N+]═C/1c2ccccc2CN1c1cc(on1)C Nature C1═NC(═O)C2═NC═[N+](C2═N1)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O Nature c1[n−]c2c(═[NH+])ncn(c2n1)C[C@@H](CO)O Nature c1nc2c(n1[C@H]1C[C@@H]([C@@H](O1)CO)O)N═CNC[C@@H]2O Nature c1nc2c(n1[C@@H]1C[C@@H]([C@@H](O1)CO)O)N═CNC[C@@H]2O Nature c1cc(ccc1C(═O)N[C@@H](CCC(═O)O)C(═O)[O−])NC[C@H]1CNC2═[N+]C(═N)N═C([O−]) Nature C2═N1 Cn1C(═O)c2nc(nn(c2nc1═O)C)c1ccc(cc1)OC Nature CCn1c2nc(═O)n(c(═O)c2nc(n1)c1ccc(cc1)OC)C Nature c1[nH]c2c(n1)c(═S)[nH]cn2 Nature c1nc2[nH]cnc2c(═O)[nH]1 Nature Cn1c(═O)c2nc(nn(c2nc1═O)C)c1ccccc1 Nature CCn1c2nc(═O)n(c(═O)c2nc(n1)c1cccs1)C Nature CCn1c2nc(═O)n(c(═O)c2nc(n1)c1cccnc1)C Nature CCn1c2nc(═O)n(c(═O)c2nc(n1)/C═C/c1ccccc1)C Nature c1nc2c(n1[C@@H]1C[C@H]([C@@H](O1)CO)O)NC═[N+]C[C@@H]2O Nature c1nc2c(n1[C@H]1C[C@H]([C@@H](O1)CO)O)NC═[N+]C[C@@H]2O Nature CCOC(═O)/C(═N/Nc1ccc(cc1)Cl)n1c(cc(nn(c1═S)C)C)[S−] Nature CCOC(═O)c1nn(c2cc(nn(c(═S)n12)C)C)c1ccc(cc1)Cl Nature Cc1c2c(c(c(c1OC)C/C═C(\C)CCC(═O)[O−])O)C(═O)OC2 Nature Cc1cc(c(c(c1C(═O)[O−])O)C)O Nature CCOC(═O)c1c(cc(cc1O)O)C Nature Cc1cc(cc(c1C(═O)OC)O)O Nature Cc1cc(c(c(c1C(═O)Oc1cc(c(c(c1C)O)C(═O)OC)C)O)C═O)O Nature Cc1cc(cc(c1C(═O)Oc1cc(c(c(c1)O)C(═O)[O−])C)O)O Nature CCCCCc1cc(c(c(c1C(═O)[O−])O)[C@H]1C═C(CC[C@@H]1C(═C)C)C)O Nature Cc1cc(c(c2c1C(═O)Oc1c(c(c3c(c1O2)[C@@H](OC3═O)O)O)C)C═O)OC Nature Cc1cc(cc(c1C(═O)Oc1cc(c(c(c1)O)C(═O)Oc1cc(c(c(c1)O)C(═O)[O−])C)C)O)O Nature CCCCCc1cc2cc(cc(c2c(═O)o1)Oc1c(cc(c(c1CCCCC)C(═O)[O−])O)O)O Nature Cc1cc(c(c(c1C(═O)[O−])O)C)OC(═O)c1c(cc(c(c1OC)C)OC)C Nature Cc1cc(cc(c1C(═O)Oc1cc(c(c(c1)O)C(═O)Oc1cc(c(c(c1)O)C(═O)[O−])C)C)O)O Nature COc1ccc(c(c1OC)O)C(═O)[O−] Nature COc1cc(c(c(c1)O)C(═O)[O−])O Nature C[C@@H]1CCCC(═O)CCCC═Cc2cc(cc(c2C(═O)O1)O)O Nature C1CCc2c(c3c(nc(nc3s2)SCCC(═O)N)N)C1 Nature COC(═O)CCSc1nc(c2c3c(sc2n1)CCCC3)N Nature C1CCc2c(c3c(s2)[n+]c(sc3═O)N)C1 Nature C1CCc2c(c3c(nc(nc3s2)SCCC(═O)N)N)C1 Nature COC(═O)CCSc1nc(c2c3c(sc2n1)CCCC3)N Nature Cn1c2c(c3c(s2)CCCC3)c(═O)n(c1═O)c1cccc(c1)Cl Nature CCOC(═O)c1c(nc2c(c1N)c1c(s2)CCCC1)C Nature Cc1nc2c(c(cs2)c2ccccc2)c(═O)n1NC(═O)c1ccccc1Cl Nature Cc1c2c(nc3n(c2═O)CCC3)sc1C(═O)NC[C@@H]1CCC[NH+]2[C@@H]1CCCC2 Nature n1c(cn(c1)C)C[C@@H](C(═O)O)N Nature Cn1cncc1C[C@@H](C(═O)[O−])[NH3+] Nature c1(c(ncn1C)S)C[C@@H](C(═O)O)N Nature c1(c(n(cn1)C)S)C[C@@H](C(═O)O)N Nature C[N@@+](C)(C)[C@@H](Cc1c[nH]c(═S)[nH]1)C(═O)[O−] Nature C[N@@+](C)(C)[C@H](Cc1c[nH]c(═S)[nH]1)C(═O)[O−] Nature c1(c(ncn1C)S)C[C@@H](C(═O)O)N(C)C Nature c1(n(cnc1)C)C[C@@H](C(═O)O)NC(═O)CCN Nature c1(n(cnc1)C)C[C@@H](C(═O)O)NC(═O)CCCN Nature n1cn(c(c1)CC(═O)O)C Nature Cn1c2c(c3c(s2)CCCC3)c(═O)n(c1═O)c1ccccc1 Nature COC(═O)CCSc1nc(c2c3c(sc2n1)CCCC3)N Nature Cn1c2c(c3c(s2)CCCC3)c(═O)n(c1═O)c1cccc(c1)Cl Nature C[C@@H](C)COc1ccccc1C(═O)NCCC(═O)[O−] Nature N1S(═O)(═O)N(C(═O)c2c1cccc2)C(C)C Nature CCOC(═O)[C@H]1C(═O)N[C@@H]2[C@@]31CCCC[C@@H]3Oc1c2cccc1 Nature CC[C@H]1CN(CC[C@H]1CC(═O)NCc1ccccc1OC)C(═O)Nc1cccc(c1)C(═O)OCC Nature c1ccc(cc1)COc1ccc2c(c1)ccn2CCC(═O)NCCC(═O)[O−] Nature c1(c(cc(c(c1)Cl)N)OC)C(═O)N[C@H]1[C@H](CN(CC1)CCCOc1ccc(cc1)F)OC Nature c12c(C(═O)N[C@H](O1)CC(═O)O)cccc2 Nature COc1ccc(cc1N)C(═O)NCCC(═O)[O−] Nature C[C@@H](C)COc1ccc(cc1)C(═O)NCCC(═O)[O−] Nature CCOC(═O)[C@@H]1C(═O)N[C@H]2[C@@]31CCCC[C@H]3Oc1c2cccc1 Nature CCC(═O)N1CC[C@]2(CCCC[C@H]2[C@H]1c1ccccc1OCC)O Nature CCCCCOc1ccc(cc1)C(═O)N1CC[C@]2(CCCC[C@H]2C1)O Nature CCOc1ccccc1[C@@H]1[C@H]2CCCC[C@@]2(CCN1C(═O)C)O Nature c1ccc(cc1)COc1ccc2ccn(c2c1)CCC(═O)N1CCC[C@@H](C1)C(═O)[O−] Nature CCCC(═O)N1CC[C@]2(CCCC[C@H]2[C@@H]1c1ccccc1OC)O Nature c12[C@@H](c3ccccc3)CC(═O)Oc1cc(c(c2)O)OC Nature [C@H]1(c2c(cc(cc2O)OC)OC(═O)C1)c1ccc(cc1)OC Nature [C@H]1(c2c(cc(cc2O)OC)OC(═O)C1)c1ccc(cc1)O Nature COc1ccc(cc1)[C@H]1CC(═O)Oc2c1c(cc(c2)O)O Nature COc1ccc(cc1)[C@@H]1CC(═O)Oc2c1c(cc(c2)O)O Nature [C@H]1(c2c(cc(c(c2)CCc2cc(c(cc2)OC)OC)O)OC(═O)C1)c1cc(c(cc1)O)O Nature c12c3c(c4c(c1CC[C@](O2)(C)C)O[C@@](CC4)(C)C)OC(═O)C[C@H]3c1cc(c(cc1)O)O Nature c12c(cc(c(c1)OC)O)CCC(═O)O2 Nature C[C@H]1CC(═O)Oc2c1ccc(c2)O Nature C[C@@H]1CC(═O)Oc2c1ccc(c2)O Nature [C@H]1([C@H]2[C@H](c3c(OC2═O)cc(cc3OC)O)c2ccc(cc2)O)[C@H](c2c(OC1═O)cc(cc2OC) Nature O)c1ccc(cc1)O c1cc(ccc1[C@@H]1c2c(cc(cc2OC(═O)[C@@H]1[C@@H]1[C@@H](c2c(c(c(c(c2OC1═O)O)O) Nature O)O)c1ccc(cc1)O)O)O)O c1cc(ccc1[C@H]1c2c(cc(cc2OC(═O)[C@@H]1[C@@H]1[C@@H](c2c(c(c(c(c2OC1═O)O)O)O) Nature O)c1ccc(cc1)O)O)O)O c1cc(ccc1[C@@H]1c2c(cc(cc2OC(═O)[C@H]1[C@@H]1[C@@H](c2c(c(c(c(c2OC1═O)O)O)O) Nature O)c1ccc(cc1)O)O)O)O c1cc(ccc1[C@H]1c2c(cc(cc2OC(═O)[C@H]1[C@@H]1[C@@H](c2c(c(c(c(c2OC1═O)O)O)O)O) Nature c1ccc(cc1)O)O)O)O c12[C@@H](c3ccccc3)CC(═O)Oc1cc(c(c2)O)OC Nature [C@H]1(c2c(cc(cc2O)OC)OC(═O)C1)c1ccc(cc1)OC Nature [C@H]1(c2c(cc(cc2O)OC)OC(═O)C1)c1ccc(cc1)O Nature COc1ccc(cc1)[C@H]1CC(═O)Oc2c1c(cc(c2)O)O Nature COc1ccc(cc1)[C@@H]1CC(═O)Oc2c1c(cc(c2)O)O Nature [C@H]1(c2c(cc(c(c2)CCc2cc(c(cc2)OC)OC)O)OC(═O)C1)c1cc(c(cc1)O)O Nature c12c3c(c4c(c1CC[C@](O2)(C)C)O[C@@](CC4)(C)C)OC(═O)C[C@H]3c1cc(c(cc1)O)O Nature c12c(cc(c(c1)OC)O)CCC(═O)O2 Nature C[C@H]1CC(═O)Oc2c1ccc(c2)O Nature C[C@@H]1CC(═O)Oc2c1ccc(c2)O Nature [C@H]1([C@H]2[C@H](c3c(OC2═O)cc(cc3OC)O)c2ccc(cc2)O)[C@H](c2c(OC1═O)cc(cc2OC) Nature O)c1ccc(cc1)O c1cc(ccc1[C@@H]1c2c(cc(cc2OC(═O)[C@@H]1[C@@H]1[C@@H](c2c(c(c(c(c2OC1═O)O)O) Nature O)O)c1ccc(cc1)O)O)O)O c1cc(ccc1[C@H]1c2c(cc(cc2OC(═O)[C@@H]1[C@@H]1[C@@H](c2c(c(c(c(c2OC1═O)O)O)O) Nature O)c1ccc(cc1)O)O)O)O c1cc(ccc1[C@@H]1c2c(cc(cc2OC(═O)[C@H]1[C@@H]1[C@@H](c2c(c(c(c(c2OC1═O)O)O)O) Nature O)c1ccc(cc1)O)O)O)O c1cc(ccc1[C@H]1c2c(cc(cc2OC(═O)[C@H]1[C@@H]1[C@@H](c2c(c(c(c(c2OC1═O)O)O)O)O) Nature c1ccc(cc1)O)O)O)O COc1ccc(cc1O)[C@H]1CC(═O)c2c(cc(cc2O1)O)O Nature COc1ccc(cc1O)[C@@H]1CC(═O)c2c(cc(cc2O1)O)O Nature COc1ccc(cc1O)[C@@H]1CC(═O)c2c(cc(cc2O1)OC)O Nature Cc1cc(c2c(c1)O[C@@H](CC2═O)c1ccc(c(c1)O)OC)O Nature COc1ccc(cc1OC)[C@H]1CC(═O)c2c(cc(cc2O1)O)O Nature COc1cc(ccc1O)[C@H]1CC(═O)c2c(cc(cc2O1)O)O Nature COc1cc(c2c(c1)O[C@@H](CC2═O)c1ccc(c(c1)O)O)O Nature c1cc(c(cc1[C@H]1CC(═O)c2c(cc(cc2O1)O)O)O)O Nature c12C(═O)C[C@H](Oc1cc(cc2O)O)c1cc(c(c(c1)O)O)O Nature c1cc(c(cc1C1CC(═O)c2c(cc(cc2O1)O)O)O)O Nature COc1cc(cc(c1OC)OC)[C@H]1CC(═O)c2c(cc(cc2O1)O)O Nature Cc1cc(c2c(c1)O[C@H](CC2═O)c1ccc(c(c1)O)OC)O Nature COc1cc(c2c(c1)O[C@H](CC2═O)c1ccc(c(c1)OC)O)O Nature COc1ccc(cc1OC)[C@H]1CC(═O)c2c(cc(cc2O1)OC)O Nature c1cc(cc(c1)O)O Nature c1c(cc(cc1O)O)O Nature O.Oc1cc(O)cc(c1)O Nature c1cc2cc3cccc(c3c(c2c(c1)O)O)O Nature c1ccc2c(c1)cc(cc2O)O Nature c1cc(c(c(c1)O)O)O Nature c1cc2cc(cc(c2c(c1)O)O)O Nature c12c(c(cc(c1)O)O)ccc(c2)O Nature c12c(cc(cc1ccc1c2c(O)ccc1)O)O Nature c1(c(ccc(c1)O)O)O Nature c1cc2cc(ccc2c(c1)O)O Nature c1cc(ccc1O)O Nature c1(c(c2c(cc1O)cccc2)O)O Nature c1ccc2cc(ccc2c1)O Nature COc1ccc(cc1O)[C@H]1CCc2ccc(cc2O1)O Nature c12c(CC[C@H](O1)c1cc(c(cc1)OC)O)ccc(c2)O Nature Cc1c(ccc2c1O[C@@H](CC2)c1ccc(c(c1)O)OC)O Nature [C@H]1(c2cc(c(cc2)O)OC)Oc2c(CC1)ccc(c2)OC Nature COc1cc(ccc1O)[C@H]1CCc2ccc(cc2O1)O Nature [C@H]1(c2cc(c(cc2)O)OC)Oc2c(CC1)ccc(c2)O Nature [C@H]1(c2cc(c(cc2)O)O)Oc2c(CC1)ccc(c2)OC Nature [C@H]1(c2cc(c(cc2)O)O)Oc2c(CC1)ccc(c2)OC Nature Cc1c(ccc2c1O[C@H](CC2)c1ccc(c(c1)O)OC)O Nature c12c(c(cc(c2)OC)O)CC[C@H](O1)c1cc(c(cc1)O)OC Nature c1cc(c(cc1[C@H]1CCc2c(cc(cc2O1)O)O)O)O Nature c12c(O[C@@H](CC2)c2cc(c(cc2)O)OC)cc(cc1OC)OC Nature c12c(c(ccc1CC[C@H](O2)c1cc(c(c(c1)O)OC)OC)OC)OC Nature COc1cc(ccc1O)[C@H]1CCc2cc(c(cc2O1)O)OC Nature c12c(O[C@@H](CC2)c2cc(c(cc2)O)O)cc(cc1OC)OC Nature COc1ccc(cc1OC)CC(═O)c1ccc(cc1O)O Nature COc1ccc(cc1OC)CC(═O)c1c(cc(cc1O)O)O Nature C[C@@H](c1ccc(c(c1)O)OC)C(═O)c1ccc(cc1O)O Nature C[C@H](c1ccc(c(c1)O)OC)C(═O)c1ccc(cc1O)O Nature C[C@@H](c1cc(cc(c1)OC)OC)C(═O)c1ccc(cc1O)O Nature COc1ccc(cc1)CC(═O)c1c(cc(cc1O)O)O Nature COc1ccc(cc1)CC(═O)c1ccc(cc1O)O Nature COc1ccc(c(c1)OC)C(═O)Cc1ccc(c(c1)OC)OC Nature CCOC(═O)CC(O)(CC(═O)OCC)C(═O)OCC Triethyl citrate VCF OC(═O)C(═O)CC1═CC═CC═C1 Phenylpyruvic VCF acid CC(═O)CCC1═CC═C(O)C═C1 4-(4- VCF Hydroxyphenyl)- 2-butanone CCOCC═C(C)C 1-Ethoxy-3- methyl-2-butene CC(C)═CCC(O)C1═CC(═O)C2═C(C(O)═CC═C2O)C1═O shikonin COC1═CC═C(C═C1O)[C@@H]1CC(═O)C2═C(O1)C═C(O[C@@H]1O[C@H] hesperidin (CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O)[C @H](O)[C@H]1O)C═C2O OC1CSC(O)CS1 1,4-Dithiane-2,5- diol CC(C)CC(═O)OCCCC1═CC═CC═C1 3-Phenylpropyl isovalerate CC1CCC(CC1)C(C)(C)OC(C)═O dihydro-alpha- VCF terpinyl acetate CCC1═C(O)C(O)═CC═C1 3-Ethyl-1,2- VCF benzenediol OC1═C(O)C═CC═C1 catechol VCF CCOC(═O)C(C)(OCC)OCC ethyl pyruvate VCF acetal CCCC[C@H]1OC(═O)C[C@H]1C cis-oak lactone VCF CCCCCCC1═CC═CC═N1 2-hexyl pyridine VCF COC1═CC(\C═C\C(\O)═C\C(═O)\C═C\C2═CC(OC)═C(O)C═C2)═CC═C1O curcumin PMN OC1═CC2═C(C(O)═C1)C(═O)C═C(O2)C1═CC(O)═C(O)C═C1 eriodictyol PMN CC1CC2(CCCCC2)OC═C1 herbal undecanol PMN C\C1═C/CCC2(C)OC2CC\C(C)═C\CC1 (E)-woody PMN epoxide CN1C2CCC1(CC(C2)OC(═O)CC(C)═S)C═O tropical 3- PMN thiobutyrate COC1═CC═C(C═C1)C(═O)OCC(O)═O 4- PMN methoxybenzoyl oxyacetic acid CCCCCC(O)CC(═O)CCC1CCC(O)C(C1)OC gingerol PMN CCOC(═O)\C═C\C1═CC═C(O)C(OC)═C1 ethyl 4-hydroxy- VCF 3-methoxy- cinnamate O═CN1CCCCC1 1- VCF Piperidinecarboxaldehyde CC1(C)C2CC1C(═C)C(═O)C2 (−)-Pinocarvone VCF CC(═O)OC1═CC═C(O)C═C1 4-Hydroxyphenyl VCF acetate NCCCCNC(N)═N Agmatine VCF COC1═CC═C(\C═C\C═C)C═C1OC \(E)-4-(1,3- VCF butadienyl)-1,2- dimethoxybenzene\ CC(C)OC1═CC═C(C)C═C1 1-isopropoxy-4- VCF methylbenzene O═CC1═NC═CN1 2- VCF imidazolecarbaldehyde CCN1CCCCC1 1-ethylpiperidine VCF CCOC(═O)COC ethyl VCF methoxyacetate COC(═O)CO methyl VCF hydroxyacetate CCOC(═O)C\C═C\C1═CC═CC═C1 ethyl 4-phenyl-3- VCF butenoate CNCC(O)═O Sarcosine CosIng CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO Sphinganine CosIng CC(═O)N[C@@H](CCC(O)═O)C(O)═O N-acetyl-L- CosIng glutamic acid CC(C)(C)[N+]([O−])═CC1═CC═[N+]([O−])C═C1 PYRIDYLOXIDET- CosIng BUTYLNITRONE OC[C@H](O)[C@H]1OC(═O)C(O)═C1OC1O[C@H](CO)[C@@H](O)[C@H] ASCORBYL CosIng (O)[C@H]1O GLUCOSIDE C\C(═C/CN(C═O)[C@@H](CC(N)═O)C(O)═O)\C═C\C═C(/C)\C═C\C1═C(C)CCCC1(C)C RETINYL CosIng FORMYL ASPARTAMATE CCCOCCC(O)O PROPOXYPROP CosIng ANEDIOL CCCCCCCCCCCCCCCCCC(═O)OC1═C(O)C(═O)O[C@@H]1[C@@H](O) ASCORBYL CosIng CO STEARATE CC1═CC═CC═C1NC(═N)NC(N)═N O-TOLYL CosIng BIGUANIDE CCCCCC[C@@H](O)C\C═C/CCCCCCCC(═O)OCC(COC(═O)CCCCCCC\C═ TRIRICINOLEIN CosIng C/C[C@H](O)CCCCCC)OC(═O)CCCCCCC\C═C/C[C@H](O)CCCCCC CCCCCCCCCCCCCCCCCCOC(═O)C(CC1═CC═C(O)C═C1)(C(C)(C)C)C(C) OCTADECYL DI- CosIng (C)C T-BUTYL-4-HYDROXY- HYDROCINNAMATE OC(═O)C1═CC═CC═C1S THIOSALICYLIC CosIng ACID OC1═C(O)C(═CC═C1)C1═CC═CC═C1 DIHYDROXYBIPHENYL CosIng NC(CCCC═O)C(O)═O Allysine FooDB OC(═O)C(═C)OP(O)(O)═O Phosphoenolpyruvic FooDB acid OCC1OC(CO)(OCC2(OCC3(OC4OC(CO)C(O)C(O)C4O)OC(CO)C(O)C3O) Nystose FooDB OC(CO)C(O)C2O)C(O)C1O CC(C)═CCCC(C)(OC1OC(COC2OCC(O)C(O)C2O)C(O)C(O)C1O)C═C L-Linalool 3- FooDB [xylosyl-(1->6)- glucoside] CC1CCC2(CCC3(C)C(═CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C Carissic acid FooDB (O)═O CCCCCC(O)CC(═O)CCC1═CC═C(O)C(OC)═C1 Gingerol FooDB CC(C)(OC1OC(CO)C(O)C(O)C1O)C1CCC(CO)(O1)C═C cis-10- FooDB Hydroxylinalyl oxide 7-glucoside CC1═C(O)C(═N)CC1 5-Imino-2-methyl- FooDB 1-cyclopenten-1- ol NCCCCCNC(N)═N Homoagmatine FooDB CC(C)═CCC1═C2OC═C(C(═O)C2═C(O)C═C1O)C1═C(O)C═C(O)C═C1 2′,4′,5,7- FooDB Tetrahydroxy-8- prenylisoflavone COC1═C(O)C2═C(C═C1)C1COC3═C(C═CC(OC)═C3O)C1O2 Melilotocarpan D FooDB CCCCCCCC1OC1CC#CC#CC(CC)OC(C)═O Ginsenoyne G FooDB COC1═CC(OC)═C(OC)C2═C1C(═O)C1═C(O2)C(OC)═C2OC(C)(C)C═CC2═ Dulxanthone G FooDB C1O CC(O)C1OC(═O)C═C1 L-erythro-5-(1- FooDB Hydroxyethyl)- 2(5H)-furanone CC(═O)C1═C2NC(═O)OC2═CC═C1 4-Acetyl-2(3H)- FooDB benzoxazolone COC1═C(OC)C═C(C═C1)C1OCC2(O)C1COC2C1═CC(OC)═C(O)C═C1 8-Hydroxy-4′- FooDB methoxypinoresinol COC1═CC═C(C═C1)C1═CC(═O)C2═C(O1)C(OC)═C(OC)C═C2O 5-Hydroxy-4′,7,8- FooDB trimethoxyflavone CC(CC(═O)\C═C(\C)C1CC(O)C2(C)C3═C(C(═O)CC12C)C1(C)CCC(═O)C(C) Ganoderenic acid A FooDB (C)C1CC3O)C(O)═O COC1═CC(═O)C2═C(C═C(C)C(C(C)═O)═C2O)C1═O 2- FooDB Methoxystypandrone CC(CC(═O)\C═C(\C)C1CC(O)C2(C)C3═C(C(═O)CC12C)C1(C)CCC(O)C(C) Ganoderenic acid C FooDB (C)C1CC3O)C(O)═O CC(═C)C1CC2═C(OC3═C(C(O)═CC4═C3C═CC(C)(C)O4)C2═O)C2═C1C(O)═ Artonol C FooDB C1OC(C)(C)C═CC1═C2O CC(OC1OC(COC(C)═O)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O)C1CC(O)C (15a,20R)- FooDB 2C3CCC4═CC(═O)CCC4(C)C3CCC12C Dihydroxypregn- 4-en-3-one 20- [glucosyl-(1->4)- 6-acetyl- glucoside] CC1═COC2═C1CC1C(═C)CCC(═O)C1(C)C2 8,12-Epoxy- FooDB 4(15)7,11- eudesmatrien-1- one CC(═C)C1CC2═CC(C(═O)CO)═C(O)C═C2O1 (S)-2,3-Dihydro- FooDB 6-hydroxy-5- (hydroxyacetyl)- 2- isopropenylbenzofuran CC1═C(O)C(C)═C2OC(CC(═O)C2═C1O)C1═CC═CC═C1 (S)-5,7- FooDB Dihydroxy-6,8- dimethylflavanone COC1═CC═CC2═C1C(CNC(═S)SC)═CN2 4- FooDB Methoxybrassinin COC1═C(CC═C(C)C)C2═C(C(O)═C1)C(═O)C1═C(O2)C(O)═C(O)C═C1 Dulxanthone A FooDB CC(CC(═O)C═C(C)C)C1CC(O)C(C)(O)C═C1 Bisacurone B FooDB COC1═CC═C(OC\C═C/C#CC2═CC═C(O)C═C2)C═C1 Asparenyol FooDB C\C(CC\C═C(/C)CCC(OC1OC(CO)C(O)C(O)C1O)C(C)(C)O)═C/CCC(C)(OC Lyciumoside III FooDB 1OC(CO)C(O)C(O)C1O)C═C CCCCCCCCCCCCCCCC\C═C\CC\C═C\CCCCCCCCCCC1═CC(C)OC1═O Muridienin 3 FooDB CC(C)CCC1═CC2═C(N1)N═CC═C2 2-(3-Methylbutyl)- FooDB 1H-pyrrolo[2,3- b]pyridine COC1═C(O)C═C(C═C1O)[C@H]1OC2═C(C[C@H]1O)C(O)═CC(O[C@@H] 4′-Methyl-(−)- FooDB 1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)═O)═C2 epigallocatechin 7-glucuronide COC1═CC2═C(C(═O)C═C(O2)C2═CC═C(O)C═C2)C(O)═C1C1OC(CO)C(O) Spinosin B FooDB C(O)C1OC1OC(COC(═O)\C═C\C2═CC(OC)═C(O)C═C2)C(O)C(O)C1O CN1CCCC1CC(═O)CC1CCC(CC(C)═O)N1C Phygrine FooDB OCC1OC(OC2C(O)C(CO)OC(OCC3OC(O)C(O)C(O)C3O)C2O)C(O)C(O)C1O Ata-D- FooDB Galactopyranosyl- (1->3)-beta-D- galactopyranosyl- (1->6)-D- galactose CCCCC\C═C\CC(O)C(O)C(═O)CCCCCCC(O)═O (9R,10S,12Z)- FooDB 9,10-Dihydroxy- 8-oxo-12- octadecenoic acid CCCCCCCCCCCCCCC1OC1CC\C═C/CCCCCCCCCCC1═CC(C)OC1═O Sabadelin FooDB COC1═C(O)C═CC(═C1)C1COC2═CC(O)═CC═C2C1 4′,7-Dihydroxy-3′- FooDB methoxyisoflavan COC1═CC2═C(C(═O)CC(O2)C2═CC(O)═C(OC)C═C2)C(OC2OC(CO)C(O)C(O)C2O)═C1 Persiconin FooDB OCC1OC(OC2═CC(O)═CC(O)═C2C(═O)CCC2═CC═CC═C2)C(O)C(O)C1O 2′,4′,6′- FooDB Trihydroxydihydrochalcone 2′- glucoside COC1═CC(═CC(O)═C1OC)C1═CC(═O)C2═C(O1)C(OC)═C(OC)C═C2 3′-Hydroxy- FooDB 4′,5′,7,8- tetramethoxyflavone COC1═CC═C(C═C1)C1COC2═C(C═CC(O)═C2)C1═O Dihydroformononetin FooDB OC1═CC(O)═C2C(═O)C(COC2═C1)C1═CC(O)═C(O)C═C1 3′,4′,5,7- FooDB Tetrahydroxyisoflavanone CC(═O)C1CCS1 xi-2- FooDB Acetylthietane COC1═CC═C(C═C1)C1═C(OC)C(═O)C2═C(OC)C(OC)═C(Cl)C(OC)═C2O1 7-Chloro- FooDB 3,4′,5,6,8- pentamethoxyflavone CC(C1CC(OC(C)═O)C2(O)C3CC4OC44C(O)C═CC(═O)C4(C)C3CCC12C)C1 Physapubenolide FooDB CC(C)═C(C)C(═O)O1 CSC1═NC(CC(C)═O)C2═C(NC3═CC═CC═C23)S1 1-[4,9-Dihydro-2- FooDB (methylthio)-1,3- thiazino[6,5- b]indol-4-yl]-2- propanone CCC1C2N3CCC22C(CC1CC3)N(C(C)═O)C1═C2C═CC═C1OC 14,19- FooDB Dihydroaspidospermatine OC(CCC(O)═O)CC1═CC═C(O)C(O)═C1 4-Hydroxy-(3′,4′- FooDB dihydroxyphenyl)- valeric acid CC1C2C(CC3C4CC═C5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(C) Avenacoside A FooDB C(O)C(O)C3O)C(O)C2OC2OC(CO)C(O)C(O)C2O)OC11CCC(C)(COC2OC (CO)C(O)C(O)C2O)O1 COC1═CC(═CC(O)═C1OC)C(O)═O 3,4-O- FooDB Dimethylgallic acid CC\C═C/C\C═C/C\C═C/CCCCCCCC(═O)OCC(O)COC1OC(COC2OC(CO)C Gingerglycolipid A FooDB (O)C(O)C2O)C(O)C(O)C1O C\C═C\S(═O)CC(NC(═O)CCC(N)C(O)═O)C(O)═O gamma- FooDB Glutamyl-S-(1- propenyl)cysteine sulfoxide CC1(C)CC(O)C2(C)CCC3(C)C(═CCC4C5(C)CCC(O)C(C)(C═O)C5CCC34C) Sandosapogenol FooDB C2C1 OC(C(O)═O)C(O)═O Hydroxypropane FooDB dioic acid CC1(C)CCCC2(C)C(\C═C\C(═C)C(O)CO)C(C)(O)C(O)C(O)C12 Sterebin G FooDB COC1═CC(\C═C\C(═O)O[C@@]2(C[C@@H](O)[C@H](O)[C@@H](C2)OC 1-Feruloyl-5- FooDB (═O)\C═C\C2═CC(O)═C(O)C═C2)C(O)═O)═CC═C1O caffeoylquinic acid [H][C@@]12O[C@]3([H])C═C(C)C(═O)C[C@]3(COC(C)═O)C(C)([C@H](OC 8- FooDB (C)═O)[C@H]1O)C21CO1 Oxodiacetoxyscirpenol CC(C)═C1CCC2(C)CCC═C(C)C2C1 3,7(11)- FooDB Eudesmadiene COC1═C(\C═C/C(═O)C2═CC═C(O)C═C2)C═C(C(O)═C1)C(C)(C)C═C Licochalcone A FooDB CCS(═O)CC(N)C(O)═O Ethiin FooDB NC1═CC2═NC3═CC═CC═C3OC2═CC1═O Questiomycin A FooDB CC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1═CC(═O)C(C)═C(C)C1═O gamma- FooDB Tocopheryl quinone ONC(═O)OCC1C2NC(═N)NC22N(CCC2(O)O)C(═N)N1O N′- FooDB Hydroxyneosaxitoxin COC1═CC═CC(OC)═C1C1═CC(═O)C2═C(O1)C═CC(OC)═C2OC Zapotin FooDB COC1═CC(OC)═C2C(OC3═C2C(═O)OC2═C3C═CC(O)═C2)═C1 Wairol FooDB CC(CCC1(O)OC2CC3C4CC(O)C5CC(OC6OC(CO)C(OC7OC(CO)C(O)C(O Ampeloside Bf1 FooDB C8OC(CO)C(O)C(O)C8O)C7O)C(O)C6O)C(O)CC5(C)C4CCC3(C)C2C1C)C OC1OC(CO)C(O)C(O)C1O CC(═C)C1CCC2(C)CCC(═O)C(C)═C2C1 (+)-4,11- FooDB Eudesmadien-3- one CCCCCC(═O)CCOC1OC(CO)C(O)C(O)C1O 1-(beta-D- FooDB Glucopyranosyloxy)- 3-octanone COC1═CC═C(O)C2═C1CC(C(C)═C)C(C)(C2)C═C Flavidulol B FooDB CC(═O)C1═C2OC3═C(C(O)═CC4═C3C═CC(C)(C)O4)C(═O)C2═CC2═C1C Artonol B FooDB (═O)OC2(C)C CCCCCCCCCCC1OC(CCC1O)C(O)CCC(O)C1CCC(CCCCCCCC(O)CC2═ Mucocin FooDB CC(C)OC2═O)O1 CC1OC(OCC2OC(OC3═C(OC4═CC(O)═CC5═[O+]C(C)═CC3═C45)C3═CC Pyranodelphinin A FooDB (O)═C(O)C(O)═C3)C(O)C(O)C2O)C(O)C(O)C1O CC(C)C1═C2C3═CC═C(CC(OC4OCC(O)C(O)C4O)C3(C)CCC2(C)CC1)C═O Erinacine A FooDB OCC1OC(OC2═CC═C(\C═C\C(═O)OCC3CCN4CCCC34)C═C2)C(O)C(O)C1O Thesinine 4′-O- FooDB glucoside CCCCCC(O)CCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCC1═C Atemoyacin B FooDB C(C)OC1═O COC1═C(C═CC(O)═C1)C1COC2═C(C1)C═CC(O)═C2 Isovestitol FooDB CC1C(C)C(═O)OC1C(O)C(C)(O)C1C(O)CC2C3CC4OC44C(O)C═CC(═O)C Ixocarpalactone A FooDB 4(C)C3CCC12C COC1═CC(═CC═C1O)[C@H]1COC2═CC(O)═CC═C2C1 3′-O-Methylequol FooDB O[C@H]1[C@H](OC2═C(O)C═C(\C═C\C(O)═O)C═C2)O[C@@H]([C@@H] Caffeic acid 4-O- FooDB (O)[C@@H]1O)C(O)═O glucuronide CC1OC(CC(O)C1O)OC1CCC2(C═O)C3CCC4(C)C(CCC4(O)C3CCC2(O)C1) Corchoroside A FooDB C1═CC(═O)OC1 CC1OC(OC2C(O)C(O)COC2OC(═O)C23CCC(C)(C)CC2C2═CCC4C5(C)CC Medicagenic acid FooDB (O)C(O)C(C)(C5CCC4(C)C2(C)CC3)C(O)═O)C(O)C(O)C1OC1OCC(O)C(O) 28-O-[b-D- C1O xylosyl-(1->4)-a- L-rhamnosyl-(1-> 2)-a-L- arabinosyl] ester OC1COC(OC2C3C4═C(O)C═C(O)C═C4OC2(OC2═CC(O)═C4CC(O)C(OC4═ 3-O-alpha-L- FooDB C32)C2═CC═C(O)C(O)═C2)C2═CC═C(O)C(O)═C2)C(O)C1O Arabinopyranosyl proanthocyanidin A5′ CC12CC(O)CC(C)(C1C(C(O)═O)C13CC(CCC21)C(═C)C3)C(O)═O Gibberellin A110 FooDB O═C1C2C(COC3═CC4═C(OCO4)C═C23)OC2═C1C═C1C═COC1═C2 Dolineone FooDB CC1OC(CC(O)C1OC1OC(CO)C(O)C(O)C1O)OC1CCC2(C)C(CCC3C2C(O) Corchorusoside B FooDB CC2(C)C(CCC32O)C2═CC(═O)OC2)C1 CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCC(O)CCCCCCC(O)CC1═CC Rolliacocin FooDB (C)OC1═O OCC1OC(C(O)C(O)C1O)C1═C(O)C═C(O)C2═C1OC1═C(C═C(O)C(O)═C1) Isomangiferin FooDB C2═O COC1═C(O)C═C(C(OC2OC(CO)C(O)C(O)C2O)═C1)C1═COC2═CC(O)═C Licoagroside A FooDB (OC)C═C2C1═O CC(C)C(C)\C═C\C(C)C1CCC2C3═CC(═O)C4═CC(═O)CCC4(C)C3CCC12C Ganodosterone FooDB CC1═C(O)C═C2C(═O)C(O)C3CCC(O)C(O)C3C2═C1 Solanolone FooDB OCC1OC(C(O)C(O)C1O)C1═C(O)C(OC2═CC═C(C═C2)C2CC(═O)C3═C(O) Occidentoside FooDB C═C(O)C═C3O2)═C(O)C(C(═O)\C═C\C2═CC═C(O)C═C2)═C1O CC(C)CC(═O)O[C@@H]1C[C@@H]2CC[C@@]1(C)C2(C)C Bornyl FooDB isovalerate CCCCC1═NC2═CC═CC═C2N1 2-Butyl-1H- FooDB benzimidazole CC(═O)OCC12CC(OC(═O)CC(C)(C)O)C(C)═CC1OC1C(O)C(OC(C)═O)C2 3′-Hydroxy-T2 FooDB (C)C11CO1 Toxin COC1═C(OC2OC(C)C(O)C(O)C2O)C═C(O)C2═C1OC═C(C2═O)C1═CC═C Isotectorigenin 4′- FooDB (OC2OC(CO)C(O)C(O)C2O)C═C1 glucoside 7- rhamnoside COC1═CC═C(\C═C\C2═CC(OC)═CC(═O)O2)C═C1 Yangonin FooDB OCC1OC(OC2═CC(O)═C3C(═O)C(═COC3═C2)C2═CC═CC═C2O)C(O)C(O) Isogenistein 7- FooDB C1O glucoside CC(O)C(C)OC1OC(CO)C(O)C(O)C1O 2,3-Butanediol FooDB glucoside CC(C)CNC(═O)\C═C\CC\C═C\C1═CC2═C(OCO2)C═C1 (E,E)-Futoamide FooDB CCCCCC1═NC(CCC)═CS1 2-Pentyl-4- FooDB propylthiazole COC1═C(O)C═CC(═C1)C1OCC(CC2═CC3═C(OCO3)C═C2)C1CO Sanshodiol FooDB CC1═C(C═C)C(═O)NC1CC1═C(C)C(CCC(O)═O)═C(N1)C1C(C(O)═O)C(═O) Brassica napus FooDB C2═C1NC(CC1═C(CCO)C(C)═C(N1)C═O)═C2C non-fluorescent chlorophyll catabolite 3 CC(C)(CS(O)(═O)═O)NC(═O)C═C 2-Methyl-2-[(1- FooDB oxo-2- propenyl)amino]- 1- propanesulfonic acid CC1═CC2═C(C(═O)C(C)(CO)C2)C(C)═C1CCCl (S)-Pterosin K FooDB CC1(C)OC2═CC(═CC(O)═C2C═C1)C1═CC2═C(O1)C═C(O)C═C2 Moracin D FooDB CC(C\C═C\C(C)(C)OC1OC(CO)C(O)C(O)C1O)C1CCC2(C)C3C═CC45OCC Goyaglycoside e FooDB 3(CCC12C)C4CCC(OC1OC(CO)C(O)C(O)C1O)C5(C)C COC1═C(O)C2═C(OC(═CC2═O)C2═CC(OC3OC(CO)C(O)C(O)C3O)═C(O) 6-Methoxyluteolin FooDB C═C2)C═C1O 3′-glucoside NCCCCNCCCNCCCCNCCCN 1,17-Diamino- FooDB 4,9,13- triazaheptadecane CC1(C)CCC2(CCC3(C)C(═CCC4C5(C)CCC(OC6OCC(O)C(OC7OC(CO)C(O)C Elatoside E FooDB (O)C7O)C6OC6OCC(O)C(O)C6O)C(C)(C)C5CCC34C)C2C1)C(O)═O COC1C2═C(C(O)═C(O)C(═C2)C(C)C)C23CCCC(C)(C)C2C1(OC)OC3═O 6,7-Dimethoxy-7- FooDB epirosmanol CC(O)CC1═CC(═O)C2═C(O1)C═C(OC1OC(CO)C(O)C(O)C1O)C═C2C Aloesol 7- FooDB glucoside COC1═C(O)C═C2C(═O)OC3═C4C(═CC(OC5OC(CO)C(OC6OC(CO)C(O)C 3-Methylellagic FooDB (O)C6O)C(O)C5O)═C3OC)C(═O)OC1═C24 acid 2-(4- galactosylglucoside) CC1(O)CCC(O)C2(C)CCC3C(OC(═O)C3═C)C12 1alpha- FooDB Hydroxyarbusculin A CC1C2C(CC3C4CCC5CC(CCC5(C)C4CCC23C)OC2OC(COC3OC(C Parillin FooDB O)C(O)C(O)C3O)C(OC3OC(C)C(O)C(O)C3O)C(O)C2OC2OC(CO)C(O)C(O)C2 O)OC11CCC(C)CO1 CC(C)═CCC\C(C)═C\CC\C(C)═C\CC\C(C)═C\CC\C(C)═C\CC\C(C)═C\CC\ Arachisprenol 12 FooDB C(C)═C\CC\C(C)═C\CC\C(C)═C/CC\C(C)═C/CC\C(C)═C\CC\C(C)═C\CO COC1═C(O)C═CC(CC(COC2OC(COC(═O)CC(C)(O)CC(O)═O)C(O)C(O)C (8R,8′R)- FooDB 2O)C(COC2OC(COC(═O)CC(C)(O)CC(O)═O)C(O)C(O)C2O)CC2═CC(OC)═ Secoisolariciresinol C(O)C═C2)═C1 9,9′-bis-[4- carboxy-3- hydroxy-3- methylbutanoyl-(->6)- glucoside] CC(C)(OC1OC(CO)C(O)C(O)C1O)C1CC2═C(O1)C═C1OC(═O)C═CC1═C2O Celereoside FooDB COC1═CC2═C(C(O)═C1CC═C(C)C)C(═O)C1═C(O)C═CC(OC)═C1O2 1,8-Dihydroxy-3,5- FooDB dimethoxy-2- prenylxanthone CC(C)(OO)\C═C\CC(C)(OC1OC(CO)C(O)C(O)C1O)C1CCC2(C)C1C(O)CC Notoginsenoside E FooDB 1C3(C)CCC(OC4OC(CO)C(O)C(O)C4OC4OC(CO)C(O)C(O)C4O)C(C)(C) C3CCC21C OCC1C(COC1C1═CC2═C(OCO2)C═C1)C(═O)C1═CC2═C(OCO2)C═C1 8′-Episesaminone FooDB CC1CC(C)(C)CC1═O 2,4,4- FooDB Trimethylcyclopentanone CCCCCCCCCCCCCCCC(═O)OC1═CC═C(CC═C)C═C1OC Oryzarol FooDB CCCC1═CC(═O)OC2═C1C(O)═C(CC═C(C)C)C(O)═C2C(═O)CC(C)C Mammea B/BA FooDB OCC1OC(C(O)C(O)C1O)C1═C(O)C(C2OCC(O)C(O)C2O)═C2OC(═CC(═O) 6-beta-D- FooDB C2═C1O)C1═CC═C(O)C═C1 Glucopyranosyl-8- beta-D- ribopyranosylapigenin [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)[C@H] 6- FooDB (O)C[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@@H](O)[C@H](O)[C Deoxocastasterone @@H](C)C(C)C CC(C)═CCC1CC23CC(CC═C(C)C)C(C)(C)C(CC═C(C)C)(C(═O)C(C(═O)C4═ (+)- FooDB CC(O)═C(O)C═C4)═C2OC1(C)C)C3═O Isoxanthochymol CCCCCC(O)CC(CCC1═CC(OC)═C(O)C═C1)OC(C)═O [6]-Gingerdiol 3- FooDB acetate CCCCC(O)CCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCCCC Asiminocin FooDB 1═CC(C)OC1═O OC1═CC═CC2═C(O)C═CC(O)═C12 1,4,5- FooDB Naphthalenetriol COC1═CC═CC2═C1NC1═C2C═C(CO)C═C1 Mukoline FooDB COC(C1C(C(O)C(═O)N1C)C1═CC═CC═C1)C1═CC═CC═C1 Lansimide 3 FooDB OC1═CC(O)═C2C(C(OC(═O)C3═CC(O)═C(O)C(O)═C3)C(OC2═C1)C1═CC═ ent-Epicatechin- FooDB C(O)C(O)═C1)C1═C2OC(C(CC2═C(O)C═C1O)OC(═O)C1═CC(O)═C(O)C (4alpha->8)-ent- (O)═C1)C1═CC═C(O)C(O)═C1 epicatechin 3,3′- digallate CN1C(CC(C)═O)C2═C(C═CC3═C2OCO3)C2═C1C1═CC3═C(OCO3)C═C1 xi-8- FooDB C═C2 Acetonyldihydrosanguinarine CC(═C)C1CC(═O)C2═C(C1)C(═O)C1═C(O2)C2═C(OC(C)(C)C═C2)C═C1O Artonol A FooDB CC1═C(OC2OC(COC(═O)CC(C)(O)CC(O)═O)C(O)C(O)C2O)C(═O)C═CO1 Licoagroside B FooDB OC1═CC(O)═C2CC(OC(═O)C3═CC(O)═C(O)C(O)═C3)C(OC2═C1)C1═CC Theaflavin 3,3′- FooDB (O)═C(O)C2═C1C═C(C═C(O)C2═O)C1OC2═CC(O)═CC(O)═C2CC1OC(═O) digallate C1═CC(O)═C(O)C(O)═C1 CCC1═C(O)C(═N)CC1 2-Ethyl-5-imino-1- FooDB cyclopenten-1-ol CC(C(═O)C1═C(O)C═C(O)C(O)═C1)C1═CC═C(O)C═C1 5′-Hydroxy-O- FooDB desmethylangolensin COC1═CC(═CC(OC)═C1O)C12OC(C)(C(C1OC1OC(CO)C(O)C(O)C1O)C1═ 5′- FooDB C(O)C═C(O)C═C1O2)C(C)═O Methoxycastavinol CC1CCC2═C(C3═C(OC═C3C)C═C2C)C1═O (S)-Curzeone FooDB COC1═CC═C(C═C1)C1═CC(═O)C2═C(OC)C═C(OC)C═C2O1 4′,5,7- FooDB Trimethoxyflavone CC(C)(OC1OC(CO)C(O)C(O)C1O)C1═CC2═C(O1)C═CC1═C2OC(═O)C═C1 Edulisin VI FooDB CCCCCCCCCCC(O)C1CCC(O1)C(O)CCC(O)C1CCC(CCCCCCCCCC2═C Squamostatin E FooDB C(C)OC2═O)O1 CC1C2CCC(C)CN2C2CC3C4CC═C5CC(CCC5(C)C4CCC3(C)C12)OC1O gamma- FooDB C(CO)C(O)C(O)C1O Chaconine CC1(C)C2CCC3(C)C(CC═C4C5CC(C)(CCC5(C)CCC34C)C(O)═O)C2(C)C Katononic acid FooDB CC1═O COC1═CC2═C(C(═O)C═C(O2)C2═CC═C(O)C═C2)C(O)═C1C1OC(CO)C(O) Spinosin C FooDB C(O)C1OC1OC(COC(═O)\C═C\C2═CC═C(O)C═C2)C(O)C(O)C1O CC1(C)CC(O)C2(CO)C(O)CC3(C)C(═CCC4C5(C)CCC(O)C(C)(C═O)C5CC Camelliagenin B FooDB C34C)C2C1 COC1═CC2═C(C3C═COC3O2)C2═C1C(═O)C1═C(O2)C(OC)═C(OC)C═C1O 5,6- FooDB Dimethoxysterigmatocystin COC1═C(O)C═CC(═C1)C1═C(OC2OC(COC3OC(C(C)O)C(O)C3O)C(O)C Isorhamnetin 3-O- FooDB (O)C2O)C(═O)C2═C(O)C═C(O)C═C2O1 [b-L- rhamnofuranosyl- (1->6)-D- glucopyranoside] NCCCC(N)C(═O)NCCS(O)(═O)═O N-Ornithyl-L- FooDB taurine O═C(CC1═CC═CC═C1)OC\C═C/C1═CC═CC═C1 Cinnamyl FooDB phenylacetate OC1═CC2═C(C[C@@H](OC(═O)C3═CC(O)═C(O)C(O)═C3)[C@H](O2)C2═ (−)- FooDB CC(OC(═O)C3═CC(O)═C(O)C(O)═C3)═C(O)C(O)═C2)C(O)═C1 Epigallocatechin 3,3′-di-gallate COC1═C(O)C═C(C═C1)C1═COC2═CC(O)═CC(O)═C2C1═O Pratensein FooDB COC1═CC2═C(OCC(C2OS(O)(═O)═O)C2═C(O)C(OC)═CC(\C═C\C(O)═O)═ Torvanol A FooDB C2)C═C1 COC1═C(O)C═CC(\C═C/C(═O)OC2C(OC3═CC(O)═C4C(OC(C5═CC═C(O Kaempferol 3,4′- FooDB C6OC(CO)C(O)C(O)C6O)C═C5)═C(OC5OC(CO)C(O)C(O)C5O)C4═O)═C3) diglucoside 7-(2- OC(CO)C(O)C2O)═C1 feruloylglucoside) OCC1OC(OC2C(O)C(O)C(CO)OC2OC2═C(OC3═CC(OC4OC(CO)C(O)C Quercetin 3-(2″- FooDB (O)C4O)═CC(O)═C3C2═O)C2═CC(O)═C(O)C═C2)C(O)C(O)C1O glucosylgalactoside) 7-glucoside CC(═C)[C@H]1CC[C@@](C)(O)CC1 trans-beta- FooDB Terpineol COC1═CC(\C═C/C(═O)OC2OC(COC3OC(CO)C(O)C(O)C3O)C(OC(═O)\C═ Raphanusol A FooDB C/C3═CC(OC)═C(O)C(OC)═C3)C(O)C2O)═CC(OC)═C1O CC(C)C1═CC2═C(C═C1)C1(C)CCCC(═C)C1CC2 18-Nor- FooDB 4(19),8,11,13- abietatetraene CC1CCC(═O)C2CC3(O)OC(═O)C(C)═C3CC12C Istanbulin A FooDB CC(Cl)C(C)(O)C(═O)OC1C2═C(C)C(═O)OC2(O)CC2CCC(O)C(C)C12C 3b,8b-Dihydroxy- FooDB 6b-(3-chloro-2- hydroxy-2- methylbutanoyloxy)- 7(11)- eremophilen-12,8- olide COC1═C(O)C═C(C═C1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@ 4′-Methyl-(−)- FooDB H]1O)C(O)═O)[C@H]1OC2═C(C[C@H]1O)C(O)═CC(O)═C2 epigallocatechin 3′-glucuronide OCC1OC(OC2C(O)C(O)C(COC(═O)\C═C\C3═CC═C(OC4OC(CO)C(O)C(O) Cyanidin 3-[6-(4- FooDB C4O)C═C3)OC2OC2═C([O+]═C3C═C(O)C═C(OC4OC(CO)C(O)C(O)C4O) glucosylcoumaryl) C3═C2)C2═CC(O)═C(O)C═C2)C(O)C(O)C1O sophoroside] 5- glucoside CC(CC(═O)CC(C)C(O)═O)C1CC(O)C2(C)C3═C(C(═O)CC12C)C1(C)CCC Ganolucidic acid C FooDB (O)C(C)(CO)C1CC3 CC(C)═CCC1═C(O)C═CC(═C1)C12OC34C(OC5═C3C═CC(O)═C5CC═C(C) Licoagrodin FooDB C)OC3═CC(O)═CC═C3C4C1C(═O)C1═CC(CC═C(C)C)═C(O)C═C1O2 CCCCCCCCCCCCCCCCCCCC(═O)CC(═O)CCCCCCCCCC 11,13- FooDB Dotriacontanedione OC(═O)CC(NC(═O)C1═C(O)C═CC═C1)C(O)═O N- FooDB Salicyloylaspartic acid CC1═CC(O)═CC(O)═C1C(═O)OC1CC2(C)C3C(CC(C)(C)C3O)C═C(C═O)C 10- FooDB 12O Hydroxymelleolide CCCCC\C═C/C\C═C/CCCCCCCC(═O)CC(O)COC(C)═O Persin FooDB CCC1NC(═O)C2C(Cl)C(Cl)CN2C(═O)C(CO)NC(═O)CC(NC(═O)C(CO)NC1═ Cyclochlorotine FooDB O)C1═CC═CC═C1 CC(C)[C@@H]1CC[C@H](C)C[C@@H]1O (−)-Neoisomenthol FooDB [H][C@@]1(CC[C@@]2(C)C3═C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C Trametenolic acid B FooDB (C)(C)[C@]1([H])CC3)[C@@H](CCC═C(C)C)C(O)═O COC1═C(O)C═C(C═C1O)C1═[O+]C2═CC(O)═CC(O)═C2C═C1O[C@@H]1 4′-O- FooDB O[C@H](CO[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@ Methyldelphinidin @H](O)[C@H](O)[C@H]1O 3-O-rutinoside CC(C)(O)C\C(SC1OC(CO)C(O)C(O)C1O)═N/OS(O)(═O)═O Glucoconringiin FooDB COC(═O)CC(═O)OCC1OC(OC2═CC(O)═C3C(OC═C(C3═O)C3═CC═C(OC) Biochanin A 7-(6- FooDB C═C3)═C2)C(O)C(O)C1O methylmalonylglucoside) O═C(OC1CCCCC1)\C═C/C1═CC═CC═C1 Cyclohexyl FooDB cinnamate OC1═CC═CC(C[C@H]2COC(═O)[C@@H]2CC2═CC(O)═C(O)C═C2)═C1 4- FooDB Hydroxyenterolactone CC1═C(CO)C(═O)OC(C1)C(C)(O)C1CCC2C3CC═C4CC(CC(═O)C4(C)C3 (3b,20R,22R)- FooDB CCC12C)OC1OC(CO)C(O)C(O)C1O 3,20,27- Trihydroxy-1- oxowitha-5,24- dienolide 3- glucoside COC1═CC(O)═C2C(═O)CC(OC2═C1)C1═CC(O)═C(OC)C═C1 3′,5-Dihydroxy- FooDB 4′,7- dimethoxyflavanone CC1C2C(CC3C4CCC5CC(CCC5(C)C4CC(═O)C23C)OC2OC(CO)C(OC3O Agavoside F FooDB C(CO)C(OC4OC(CO)C(O)C(OC5OC(C)C(OC6OC(C)C(O)C(O)C6O)C(O)C 5OC5OC(C)C(O)C(O)C5O)C4OC4OCC(O)C(O)C4O)C(O)C3O)C(O)C2O) OC11CCC(C)CO1 CC1(C)CCC2(CCC3(C)C(═CCC4C5(C)CCC(OC6OCC(O)C(O)C6O)C(C)(C) 28- FooDB C5CCC34C)C2C1)C(═O)OC1OC(CO)C(O)C(O)C1O Glucosyloleanolic acid 3-arabinoside CC12OC3═C(C═CC(O)═C3)C(C1O)C1═C(OC3═C(C(O)═CC(═C3)C3═CC4═ Mulberrofuran S FooDB C(O3)C═C(O)C═C4)C1═C2)C1═C(O)C═C(O)C═C1 CC(═C)C1CCC2(CCC3(C)C(CCC4C5(C)CC(O)C(OC(═O)\C═C\C6═CC(O)═ 2alpha- FooDB C(O)C═C6)C(C)(C)C5CCC34C)C12)C(O)═O Hydroxypyracrenic acid OC1═CC═C(\C═C\C(═O)C2═CC═C(O)C═C2O)C═C1 Isoliquiritigenin FooDB COC1═CC(O)═C(C(═O)OC2CC3(C)C4C(CC(C)(C)C4O)C═C(C═O)C23O)C(C)═C1 Melleolide H FooDB CC(═O)CCC1═CC═C(OC2OC(COC(═O)C3═CC(O)═C(O)C(O)═C3)C(O)C(O)C2O)C═C1 Lindleyin FooDB CC1(C)OC2(C)CC(O)C1CC2OC1OC(CO)C(O)C(O)C1O Foeniculoside IX FooDB CCCCCCC\C═C\CCC═C (Z)-1,5- FooDB Tridecadiene CC(C)CC(O)C(═O)NC1C(OC2═CC═C(CC(NC(═O)C(CC3═CC═CC═C3)NC Vignatic acid A FooDB 1═O)C(O)═O)C═C2)C(C)C COC1═CC(OC2OC(COC3OC(CO)C(O)C(OC4OC(COC5OC(CO)C(O)C(O) Cassiaside B2 FooDB C5O)C(O)C(O)C4O)C3O)C(O)C(O)C2O)═C2C(O)═C3C(═O)C═C(C)OC3═ CC2═C1 CC(═C)[C@H]1CC[C@](C)(O)CC1 cis-beta-Terpineol FooDB COC1═C(O)C2═C(OC(═CC2═O)C2═CC(O)═C(OC3OC(CO)C(O)C(O)C3O) Eupafolin 4′- FooDB C═C2)C═C1O glucoside COC1═C(OC2OC(CO)C(O)C(O)C2O)C═CC(\C═C\C(═O)OCC2OC(OC3═C Cyanidin 3-[6-(4- FooDB ([O+]═C4C═C(O)C═C(OC5OC(CO)C(O)C(O)C5O)C4═C3)C3═CC(O)═C(O) glucosylferuloyl)sophoroside] C═C3)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)═C1 5- glucoside CC(C)CC(═O)C1═C(O)C2═C(OC3C4C(CC\C(C)═C/CCC3(C)C2)C4(C)C)C Euglobal VII FooDB (C═O)═C1O COC1═C(O)C═C(C═C1O)[C@H]1OC2═CC(O)═CC(O)═C2C[C@H]1OC(═O) 4′-Methyl-(−)- FooDB C1═CC(O)═C(OC)C(O)═C1 epigallocatechin 3-(4-methyl- gallate) CC1CCC2(CCC3(C)C(═CCC4C5(C)CC(O)C(O)C(C)(COC(═O)\C═C\C6═C 23-trans-p- FooDB C═C(O)C═C6)C5CCC34C)C2C1(C)O)C(O)═O Coumaroyloxytormentic acid O═C1CC2CCCC(C1)N2 9- FooDB Azabicyclo[3.3.1]nonan- 3-one CC(CCC═C(C)C)C1C(CC2(C)C3C(O)C═C4C(CCC(OC5OCC(OC(C)═O)C Hebevinoside XIII FooDB (OC(C)═O)C5O)C4(C)C)C3(C)CCC12C)OC1OC(COC(C)═O)C(OC(C)═O)C (O)C1O COC1═CC(CC═C)═CC(OC)═C1OC(C)C(O)C1═CC(OC)═C(OC)C(OC)═C1 2-(4-Allyl-2,6- FooDB dimethoxyphenoxy)- 1-(3,4,5- trimethoxyphenyl)- 1-propanol COC1═CC(O)═CC2═C1C(═O)C1═C(C═C(C)C(O)═C1)C2═O Cajaquinone FooDB CC(═O)C1═C(O)C═CC(O)═C1 2′,5′- FooDB Dihydroxyacetophenone OC1C(O)C2OC(═O)C3═CC(O)═C(O)C(O)═C3C3═C(O)C(O)═C(O)C═C3C Guavin B FooDB (═O)OCC2OC1OC1═CC(O)═C(C(═O)C2═CC═CC═C2)C(O)═C1 COC(═O)C1═COC(OC2OC(CO)C(O)C(O)C2O)C(C═C)C1CC(═O)OCCC1═ Oleuroside FooDB CC(O)═C(O)C═C1 COC1═CC2═C(C═C1)C═C(C(═O)O2)C(C)(C)C═C 3-(1,1- FooDB Dimethylallyl)herniarin CC(C)═CCC1═C(O)C2═C(OC(═CC2═O)C2═C(O)C═C(O)C═C2)C═C1O Artocarpesin FooDB CC1(C)CCC2(CCC3(C)C(═CCC4C5(C)CCC(OC6OCC(O)C(O)C6OC6OC Medicoside I FooDB (CO)C(O)C(O)C6OC6OCC(O)C(O)C6O)C(C)(CO)C5CCC34C)C2C1)C(═O) OC1OC(CO)C(O)C(O)C1O CC(═O)OC1(CO)COC(OC2C(O)C(O)C(CO)OC2OC2═CC═C(C═C2)C2CC Liquiritigenin 4′-[3- FooDB (═O)C3═C(O2)C═C(O)C═C3)C1O acetylapiosyl-(1-> 2)-glucoside] CC(C)CCCC(C)CCCC(C)CCC\C(C)═C\CC\C(C)═C\CO (2Z,6E)- FooDB 3,7,11,15,19- Pentamethyl-2,6- eicosadien-1-ol CC1(C)CC(O)C2(CO)C(O)CC3(C)C(═CCC4C5(C)CCC(O)C(C)(CO)C5CC Camelliagenin C FooDB C34C)C2C1 OC[C@H]1O[C@@H](OC2═CC3═C(C═C2)C(═O)C(CO3)C2═CC═C(O)C═ Dihydrodaidzin FooDB C2)[C@H](O)[C@@H](O)[C@@H]1O COC1═CC═C(\C═C\C2═CC(O)═C(OC)C(CO)═C2)C═C1O 3′-Hydroxy- FooDB 3,4,5,4′- tetramethoxystilbene OCC1OC(OC2═CC═C(\C═C\C(O)═O)C═C2)C(OC2OCC(O)(CO)C2O)C(O) cis-p-Coumaric FooDB C1O acid 4-[apiosyl-(1-> 2)-glucoside] CCC(\C═C\C(C)C1CCC2C3CC═C4CC(O)CCC4(C)C3CCC12C)C(C)═C 22- FooDB Dehydroclerosterol CC(═C)C1CCC2(CCC3(C)C(CCC4C5(C)CC(OC(═O)C6═CC(O)═C(O)C═C 2-O- FooDB 6)C(O)C(C)(C)C5CCC34C)C12)C(O)═O Protocatechuoylalphitolic acid CC(C)C(NC(═O)CCC(N)C(O)═O)C(O)═O L-gamma- FooDB glutamyl-L-valine CC1(C)CCC2(CCC3(C)C(═CCC4C5(C)CCC(OC6OC(C(OC7OC(CO)C(O) Tuberoside A FooDB C(O)C7O)C(O)C6O)C(O)═O)C(C)(C)C5CCC34C)C2C1)C(═O)OC1OC(CO) (Ullucus C(O)C(O)C1O tuberosus) CCO\C(S)═N\CC1═CC═C(O[C@@H]2O[C@@H](C)[C@H](OC(C)═O)[C@ N-[(4- FooDB @H](OC(C)═O)[C@H]2OC(C)═O)C═C1 hydroxyphenyl)methyl] ethoxycarbothioamide 4′-(tri- acetylrhamnoside) CC(C)═CCC1═C(O)C═CC(C(═O)\C═C\C2═C(O)C═C(O)C═C2)═C1O Morachalcone A FooDB OCC1OC(OC2═CC3═C(O)C═C(O)C═C3[O+]═C2C2═CC═C(O)C═C2)C(O) Pelargonidin 3- FooDB C(O)C1O galactoside COC1═CC(OC)═C(C(C)═O)C(O)═C1C 2′-Hydroxy-4′,6′- FooDB dimethoxy-3′- methylacetophenone CC1C2C(CC3C4CCC5CC(CCC5(C)C4CC(═O)C23C)OC2OC(CO)C(O)C(O Schidigerasaponin FooDB C3OCC(O)C(O)C3O)C2OC2OC(CO)C(O)C(O)C2O)OC11CCC(═C)CO1 B1 O═C1C2═CC═CC═C2C2═NC═CC3═C2C1═NC═C3 Sampangine FooDB CC(C)CCC(O)C(C)C1C(CC2C3CC═C4CC(O)CC(OC5OC(C)C(OC6OC(CO) Alliosterol 1-(4″- FooDB C(O)C(O)C6O)C(O)C5O)C4(C)C3CCC12C)OC1OC(CO)C(O)C(O)C1O galactosylrhamnoside) 16- galactoside OCC1OC(OC2C(OC3═C([O+]═C4C═C(O)C═C(OC5OC(CO)C(O)C(O)C5O) Delphinidin 3- FooDB C4═C3)C3═CC(O)═C(O)C(O)═C3)OC(CO)C(O)C2O)C(O)C(O)C1O sophoroside 5- glucoside CCCCC\C═C\CC1CC(═O)OC1═O Dihydro-3-(2- FooDB octenyl)-2,5- furandione OCC1OC(OC2═CC(O)═CC3═[O+]C(═C(OC4OC(COC(═O)\C═C\C5═CC(O)═ YGM 1B FooDB C(O)C═C5)C(O)C(O)C4OC4OC(COC(═O)\C═C\C5═CC(O)═C(O)C═C5)C (O)C(O)C4O)C═C23)C2═CC(O)═C(O)C═C2)C(O)C(O)C1O CC1═CN2C═CC═C2N═N1 3- FooDB Methylpyrrolo[1,2- a]pyrazine COC1═CC(OC2OC(CO)C(O)C(O)C2O)═C2C(OC)═C(C(C)═O)C(OC3OCC Cassitoroside FooDB (O)(CO)C3O)═CC2═C1 OC1═CC═C(\C═C/C\C═C/C2═CC(O)═CC═C2)C═C1 (1Z,4Z)-1,5-bis(4- FooDB hydroxyphenyl)- 1,4-pentadiene CC1OC(OC2C(O)C(O)C(CO)OC2OC2CCC3(C)C(CCC4(C)C3CCC3C5C6 Saponin D FooDB (CC43CO6)OC(CC5(C)OC3OC(C)C(O)C(O)C3O)C═C(C)C)C2(C)C)C(O)C (O)C1O [H][C@]12C[C@@]3([H])[C@]4([H])CC[C@]5([H])C[C@@H](O)CC[C@]5 Smilagenin FooDB (C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@@H](C) CO1)O2 CC(C)═CCC\C(C)═C/COC═O Neryl formate FooDB C\C(\C═C/C═C(/C)\C═C\C1═C(C)C(O)C(O)CC1(C)C)═C/C═C/C═C(/C)\C═C/ Idoxanthin FooDB C═C(/C)\C═C\C1═C(C)C(═O)C(O)CC1(C)C CC1(C)OC2═CC3═C(C(O)═C2C═C1)C(═O)C═C(O3)C1═C(O)C═C(O)C═C1 Cycloartocarpesin FooDB COC1═CC(O)═C(C═C1)C1═COC2═C(C(O)═CC(O)═C2OC)C1═O 5,7-Dihydroxy- FooDB 8,4′- dimethoxyisoflavone COC1═CC(═O)OC1(O)C(═O)CCCCCCC\C═C\C\C═C\CC═C 5-Hydroxy-4- FooDB methoxy-5-(1-oxo- 9,12,15- hexadecatrienyl)- 2(5H)-furanone CC1═CC2═C(C═C1O)C1(C)C(O)CC(O)(O2)C1(C)C Enokipodin C FooDB OC1═CC═C2C(═O)C(COC2═C1)C1═CC═C(O)C(O)═C1 3′- FooDB Hydroxydihydrodaidzein COC1═CC(═CC(OC)═C1O)C(O)C(C)OC1═C(OC)C═C(CC═C)C═C1OC 2-(4-Allyl-2,6- FooDB dimethoxyphenoxy)- 1-(3-hydroxy- 4,5- dimethoxyphenyl)- 1-propanol COC1═C(OC2OC(COC3OC(CO)C(O)C3O)C(O)C(O)C2O)C2═CC(═C1OC) Myricanene B 5- FooDB C1═C(O)C═CC(C\C═C\CCCC2)═C1 [arabinosyl-(1->6)- glucoside] OC1═CC═C(C═C1)C1═COC2═CC(O)═C(O)C(O)═C2C1═O 5,6,7,4′- FooDB Tetrahydroxyisoflavone OC(C(O)═O)C(O)(CC1═CC═C(O)C═C1)C(O)═O (2R,3S)-Piscidic FooDB acid COC1═CC2═C(OCO2)C═C1C1═COC2═CC(OC3OC(CO)C(O)C(O)C3OC(═ 7-Hydroxy-2′,5,6- FooDB O)\C═C/C3═CC═C(O)C═C3)═C(OC)C(OC)═C2C1═O trimethoxy-4′,5′- methylenedioxyisoflavone 7-(2-p- coumaroylglucoside) COC1═CC2═C(C(═O)C═C(O2)C2═CC═CC═C2)C(OC)═C1C Dimethylstrobochrysin FooDB COC1═C(O)C(O)═CC(═C1)C1═[O+]C2═C(C═C1O[C@@H]1O[C@H](CO[C Petunidin 3- FooDB @@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H] rutinoside (O)[C@H]1O)C(O)═CC(O)═C2 CC1OC(OCC2OC(OC3CCC4(C)C(CCC5(C)C4CCC4C6C(C)(O)C(CC═C(C) Mabioside D FooDB C)OC6(O)C(O)C54C)C3(C)C)C(O)C(O)C2O)C(O)C(O)C1O COC1═CC2═C(OC(═O)C(═C2)C(C)(C)C═C)C═C1O 3-(1,1- FooDB Dimethylallyl)scopoletin COC1═CC(O)═C2C(═O)CC(OC2═C1)C1═CC(OC2OC(CO)C(O)C(O)C2O)═ Persicogenin 3′- FooDB C(OC)C═C1 glucoside C\C(CC\C═C(/C)C(O)═O)═C/CC\C(C)═C\CCC(C)(OC1OC(CO)C(O)C(O)C1 Capsianoside IV FooDB OC1OC(CO)C(O)C(O)C1O)C═C COC(C)(C)C1═CC2═C(O1)C═CC1═C2OC(═O)C═C1 Archangin FooDB OCC(O)C(O)(CO)CO L-2- FooDB (Hydroxymethyl)- 1,2,3,4- butanetetrol OCC1OC(O)C(OC(═O)\C═C\C2═CC═C(O)C═C2)C(O)C1O 2-O-p-Coumaroyl- FooDB D-glucose OC(═O)C1═CC2═C(OCO2)C═C1 3,4- FooDB Methylenedioxybenzoic acid COC1═C(O)C2═C(C═C1)C(═O)C1═C(N2C)C2═C(OC(C)(C)C═C2)C═C1O 2′,2′- FooDB Dimethyl(pyrano- 5′,6′:3:4)-1,5- dihydroxy-6- methoxy-10- methylacridone CC(C)═CCC\C(C)═C\C═C\C(\C)═C\C═C\C(\C)═C\C═C\C═C(/C)\C═C\C═C(/ (all-E)-6′-Apo-y- FooDB C)\C═C\C═O caroten-6′-al CC1C2C3CCC4C5(C)CCC(OC(C)═O)C(C)(C)C5CCC4(C)C3(C)CCC2(C)C psi-Taraxasteryl FooDB C═C1C acetate OCC(CC1═CC(O)═C(O)C═C1)C(CO)CC1═CC═CC(O)═C1 4- FooDB Hydroxyenterodiol CC1C(C)C2(CCCO2)OC2C1OC1CC3OC4CC5OC6C\C═C/CC7OC8C═CC Pacific Ciguatoxin FooDB 9OC%10C(CC9OC8C═CC7OC6CC(O)C5(C)OC4CC(C)CC3OC1C(C)C2O) 4A OC1CC═CC(OC1C%10O)\C═C/C═C COC1═C(OC2OC(C(O)C(O)C2O)C(O)═O)C═CC(═C1)C1═C(OC)C(═O)C2═ 4′,5-Dihydroxy- FooDB C(O)C3═C(OCO3)C═C2O1 3,3′-dimethoxy- 6,7- methylenedioxyflavone 4′- glucuronide CC1C═C2C(COC2═O)C(O)C2CC(C)(C)CC12O Blennin D FooDB CC1(C)CC(═O)C2═C(O1)C═C(OC1OC(CO)C(O)C(O)C1O)C(CCC(O)═O)═ 6-(2- FooDB C2 Carboxyethyl)-7- hydroxy-2,2- dimethyl-4- chromanone glucoside CCCCCCCCCCCCCC1CC2═C(C(═O)O1)C(O)═CC═C2 (R)-3,4-Dihydro-8- FooDB hydroxy-3-tridecyl- 1H-2-benzopyran- 1-one CC(C)═CCC1═CC(═CC═C1O)C1CC(═O)C2═C(O1)C(CC═C(C)C)═C(O)C═C2 (S)-4′,7- FooDB Dihydroxy-3′,8- diprenylflavanone OC1C(COC(═O)\C═C\C2═CC═CC═C2)OC(OC(═O)C2═CC(O)═C(O)C(O)═ 6-Cinnamoyl-1,2- FooDB C2)C(OC(═O)C2═CC(O)═C(O)C(O)═C2)C1O digalloylglucose CC(O)CC(═O)CC1═CC(OC2OC(CO)C(O)C(O)C2O)═CC2═C1C(═O)C═C(C) 7-Hydroxy-5-(4- FooDB O2 hydroxy-2- oxopentyl)-2- methylchromone 7-glucoside CCCCCCCOC(═O)\C═C/C1═CC═CC═C1 Heptyl cinnamate FooDB COC1═CC2═C(C═C1)C(═O)C(═C(C)O2)C1═CC═CC═C1 7-Methoxy-2- FooDB methylisoflavone COC1═CC2═C(OC3═C2C(C)═CC(OC)═C3O)C(═C1)C(O)═O Porric acid A FooDB CC(C)═CCC\C(C)═C\CC1═C(O)C2═C(OC3═C(C═CC═C3O)C2═O)C═C1O Mangostinone FooDB CC1OC(OC2C(O)C(OC(OC3CCC4(C)C(CCC5(C)C4CC═C4C6CC(C)(C)C Quillaic acid 3- FooDB CC6(C(O)CC54C)C(═O)OC4OC(C)C(OC(C)═O)C(OC5OC(CO)C(O)C(O)C [galactosyl-(1->2)- 5O)C4OC4OC(C)C(OC5OCC(O)C(O)C5O)C(O)C4O)C3(C)C═O)C2OC2O [rhamnosyl-(1-> C(CO)C(O)C(O)C2O)C(O)═O)C(O)C(O)C1O 3)]-glucuronide]28- [glucosyl-(1-> 3)-[xylosyl-(1-> 4)-rhamnosyl-(1-> 2)]-4-acetyl- fucosyl] ester CC(C1CC(C)═C(C)C(═O)O1)C12OC1C(OC(C)═O)C1(O)C3CC4OC44C(O) Physagulin C FooDB C═CC(═O)C4(C)C3CCC21C NC1═CC═CC═C1C(═O)OC1═CC2═CC═CC═C2C═C1 2-Naphthalenol 2- FooDB aminobenzoate CC\C═C/C1═CC2═C(C═CC═C2O)C(═O)O1 Artemidinol FooDB [H][C@@]12[C@H](O)C(C)(C)CC[C@@]1(CC[C@]1(C)C2═CCC2[C@@]3 28- FooDB (C)CC[C@H](O[C@@H]4OC[C@H](O)[C@H](O)[C@H]4O)C(C)(C)C3CC Glucosylsiaresinolate [C@@]12C)C(═O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O 3-arabinoside CC(CCC(C)C(C)═C)C1CCC2(C)C3CCC4CC(═O)CCC44CC34CCC12C 28- FooDB Norcyclomusalenone CC1C2C(CC3C4CC═C5CC(OC6OC(CO)C(OC7OC(CO)C(O)C(OC8OC(C Fistuloside C FooDB O)C(O)C(O)C8O)C7O)C(O)C6O)C(O)CC5(C)C4CCC23C)OC11CCC(C)C O1 CC(C(═O)C1═C(O)C(O)═C(O)C═C1)C1═CC═C(O)C═C1 3′-Hydroxy-O- FooDB desmethylangolensin COC1═CC(C(═O)C(C)C2═CC═C(O)C═C2)═C(O)C═C1O 5′-Methoxy-O- FooDB desmethylangolensin CC(O)C#CC1═C(C)CC(CC1(C)C)OC1OC(CO)C(O)C(O)C1O 5-Megastigmen-7- FooDB yne-3,9-diol 3- glucoside COC1═CC2═C(C═CC(═O)O2)C═C1C 7-Methoxy-6- FooDB methyl-2H-1- benzopyran-2-one CC(C)═CCCC(C)(OC1OC(COC2OCC(O)C(O)C2O)C(O)C(O)C1O)C1CCC Notoginsenoside FooDB 2(C)C1C(O)CC1C3(C)CCC(OC4OC(CO)C(O)C(O)C4OC4OC(CO)C(O)C Fc (O)C4OC4OCC(O)C(O)C4O)C(C)(C)C3CCC21C CC(C)C(C)CCC(C)C1CCC2(C)C3CCC4C(C)C(═O)CCC44CC34CCC12C Cycloeucalanone FooDB CC(═O)OC1C(OC2OCC(O)C(O)C2O)C(OC2CCC3(C)C(CCC4(C)C3CC═C Goyasaponin III FooDB 3C5CC(C)(C)CCC5(CCC43C)C(O)═O)C2(C)C)OC(C1OC1OC(CO)C(O)C (O)C1O)C(O)═O CC(C)═CC1OC2═C(C═CC(O)═C2)C2═C1C(═O)C1═C(O)C═C(O)C═C1O2 Cyclocommunol FooDB CC(C)═CCCC(C)(OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)C1 Notoginsenoside FooDB CCC2(C)C1C(O)CC1C3(C)CCC(OC4OC(CO)C(O)C(O)C4OC4OC(CO)C Fa (O)C(O)C4OC4OCC(O)C(O)C4O)C(C)(C)C3CCC21C OC(C1OC(═O)C(O)C1OC(═O)C1═CC(O)═C(O)C(O)═C1)C(O)═O 3-O-Galloyl-1,4- FooDB galactarolactone OC1COC2(OC3(O)CC45C2OC2(O)C4C4═C(OC32O)C(O)═C(O)C═C4C(═ Putranjivain A FooDB O)OC2C(OC(═O)C3═CC(O)═C(O)C(O)═C3)OC3COC(═O)C4═CC(O)═C(O) C(O)═C4C4═C(O)C(O)═C(O)C═C4C(═O)OC2C3OC5═O)C1O [OH+]([Hg]C1═CC═CC═C1)[Hg]C1═CC═CC═C1 m- FooDB Hydroxydiphenyldimercury (1+) OC1═CC2═C(C═C1)C1═C(C3═CC4═C(OCO4)C═C3O1)C(═O)O2 Medicagol FooDB COC1═CC(═CC(O)═C1OC)C1CCC2═C(O1)C(O)═C(OC)C═C2C1═CC(OC)═ 5′,5′″,8,8″- FooDB C(O)C2═C1CCC(O2)C1═CC(O)═C(OC)C(OC)═C1 Tetrahydroxy- 3′,3′″,4′,4′″,7′,7″- hexamethoxy- 5,5″-biflavan CC(C)═CC(═O)OC1C(OC2═C1C1═C(C═C2)C═CC(═O)O1)C(C)(C)OC(═O)\ Edulisin I FooDB C═C\C1═CC═C(O)C═C1 COC1═C([O−]) 15-Epibetanidin 5- FooDB C═CC(\C═C\C(═O)OC2(CO)COC(OC3C(O)C(O)C(CO)OC3OC3═C(O)C═ [E-feruloyl-(->3)- C4C(CC(C(O)═O)\[N+]4═C\C═C4/CC(NC(═C4)C(O)═O)C(O)═O)═C3)C2O)═ apiosyl-(1->2)- C1 glucoside] COC1═CC(OC)═C(C(═O)C2═CC═CC═C2)C(OC)═C1 2,4,6- FooDB Trimethoxybenzophenone COC1═CC(CC═C)═CC(OC)═C1OC(C)C(OC(C)═O)C1═CC2═C(OCO2)C═C1 1-(2H-1,3- FooDB Benzodioxol-5-yl)- 2-[2,6-dimethoxy- 4-(prop-2-en-1- yl)phenoxy]propyl acetate COC1═C2CC(COC2═CC2═C1CCC(C)(C)O2)C1═C(O)C(CC═C(C)C)═C(O) Kanzonol H FooDB C═C1 COC1═CC2═C(CC(CO2)C2═C3OC(C)(C)C═CC3═C(O)C═C2)C(OC)═C1C Kanzonol I FooDB C═C(C)C CN1CCCCC1CC(═O)C1═CC═C(O)C═C1 Thalictroidine FooDB COC1═CC(═CC═C1O)C1OC(C(C)C1C)C1═CC(OC)═C(OC)C(OC)═C1 Fragransin D1 FooDB COC1═C(O)C(O)═C2C(═O)C═C(OC2═C1)C1═CC(O)═C(O)C═C1 2-(3,4- FooDB Dihydroxyphenyl)- 5,6-dihydroxy-7- methoxy-4H-1- benzopyran-4-one COC(═O)CCC1(C)C2CC3═C(OC2(C)CC(O)C1C(C)(C)O)C(C)═C1COC(═O) Austalide H FooDB C1═C3OC CC(C)═CCC1═C(OC2═C(C(O)═C3CC(OC3═C2)C(C)(C)O)C1═O)C1═C(O) Mulberranol FooDB C═C(O)C═C1 OCC1OC(C(O)C(O)C1O)C1C2═C(C(O)═C(O)C═C2)C(═O)C2═C1C═C(CO) 7-Hydroxyaloin B FooDB C═C2O COC1═C(C═CC(O)═C1CC═C(C)C)C1COC2═C(C1)C═CC(O)═C2 4′,7-Dihydroxy-2′- FooDB methoxy-3′- prenylisoflavan CC12CC(O)CC3(OC1═O)C1CCC4(O)CC1(CC4═C)C(C23)C(O)═O Gibberellin A81 FooDB CCCC1═CC(═O)OC2═C(C(═O)CC(C)C)C(O)═C3C4OOC(C)(C)C4OC3═C12 6-Hydroxy-9,9- FooDB dimethyl-5-(3- methyl-1- oxobutyl)-1- propyl-3H,9H- [1,2]- dioxolo[3′,4′:4,5]furo [2,3- f][1]benzopyran-3- one C\C═C/SCC(N)C(O)═O trans-S-(1- FooDB Propenyl)-L- cysteine CC(C)═CCC1═C2OC(C)(C)C═CC2═C(O)C2═C1OC1═C(C(OC3═C1C═C(O) Cycloheterophyllin FooDB C(O)═C3)C═C(C)C)C2═O CCC(CCC(C)C1CCC2C3═CCC4CC(O)CCC4(C)C3CCC12C)═C(C)C Peposterol FooDB CC1═CC2═C(C(═O)C(C)(CO)C2)C(C)═C1CCOC1OC(CO)C(O)C(O)C1O Pteroside A FooDB CC(C)═CCCC(COC1OCC(O)C(O)C1O)C1CCC2(C)C3═C(CCC12C)C1(C) Tsugarioside B FooDB CCC(OC(C)═O)C(C)(C)C1CC3 COC1═CC(═CC═C1O)C1═C(OC2OC(COC3OC(CO)C(O)C(O)C3O)C(O)C Spinacetin 3- FooDB (O)C2O)C(═O)C2═C(O1)C═C(O)C(OC)═C2O gentiobioside COC1═CC(CC(CO)C(CO)CC2═CC3═C(OCO3)C═C2)═CC(OC)═C1OC Dihydroclusin FooDB COC1C═C2C(CCC(OC3OCC(O)C(O)C3O)C2(C)C)C2(C)CCC3(C)C(C(C)C Hebevinoside XI FooDB CC═C(C)C)C(CC3(C)C12)OC1OC(COC(C)═O)C(OC(C)═O)C(O)C1O COC1═C(C(O)═C(C(═O)C2═CC═CC═C2)C(O)═C1)C1═CC(O)═C2OC3═C Garciduol A FooDB (C═CC═C3O)C(═O)C2═C1O OCC1═CNC2═NC(═O)NC(═O)C2═N1 6- FooDB (Hydroxymethyl)- 2,4(1H,3H)- pteridinedione COC1═C(O)C═CC(CCC(O)CC(═O)CCC2═CC═CC═C2)═C1 5-Hydroxy-7-(4- FooDB hydroxy-3- methoxyphenyl)-1- phenyl-3- heptanone OCC1OC(OC2═CC(O)═CC3═[O+]C(═C(OC4OC(COC(═O)\C═C\C5═CC(O)═ YGM 1A FooDB C(O)C═C5)C(O)C(O)C4OC4OC(COC(O)═C5C═CC(═O)C═C5)C(O)C(O)C 4O)C═C23)C2═CC(O)═C(O)C═C2)C(O)C(O)C1O OCC1OC2C(OC(═O)N2C2═CC═CC═C2O)C(O)C1O Hexahydro-6,7- FooDB dihydroxy-5- (hydroxymethyl)- 3-(2- hydroxyphenyl)- 2H-pyrano[2,3- d]oxazol-2-one C\C═C(/C)C(═O)OC1C(O)C(C)(C)CC2C3═CCC4C5(C)CCC(O)C(C)(C═O) (3b,16a,21b,22a)- FooDB C5CCC4(C)C3(C)CC(O)C12CO 12-Oleanene- 3,16,21,23,28- pentol-22- angeloyloxy-23-al COC1═C(OC)C═C(C═C1)C1═C(O)C(═O)C2═C(O)C═C(O)C═C2O1 3′,4′-Di-O- FooDB methylquercetin CC1═CC(═O)C2C(C)(C)C(O)CCC2(C)C1COC1═CC2═C(C═CC(═O)O2)C═ (3′x,5′a,9′x,10′b)- FooDB C1 O-(3-Hydroxy-6- oxo-7-drimen-11- yl)umbelliferone CC12CCCC(C)(C1C(O)C(O)C13CC(O)(COC4OC(CO)C(O)C(O)C4O)C(O) Canavalioside FooDB (C1)CCC23)C(O)═O COC1═C(O)C═CC(═C1)C1OC2═C(C═C(C═C2O)C2OC3═CC(O)═CC(O)═C Silicristin FooDB 3C(═O)C2O)C1CO COC1═C(O)C2═C(C(CC═C(C)C)═C1)C(═O)C1═C(O2)C(CC═C(C)C)═C(O Dulxanthone C FooDB C)C═C1O CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCC(═O)CCCCCCC(O)CC1═C Reticulacinone FooDB C(C)OC1═O COC1═C(O)C═CC(\C═C\C(═O)OC(C(O)═O)C(O)(CC(O)═O)C(O)═O)═C1 2-O- FooDB Feruloylhydroxycitric acid OCCCCCCCC\C═C\C(O)C#CC#C 9-Pentadecene- FooDB 12,14-diyne-1,11- diol OCC1OC(OC2C(O)C(O)C(CO)OC2C2═C(O)C3═C(OC(═CC3═O)C3═CC═ Meloside L FooDB C(O)C(O)═C3)C═C2O)C(O)C(O)C1O COC1═C(O)C═C(O)C2═C1OC(C1═CC═C(O)C═C1)═C(OC1OC(CO)C(O)C Sexangularetin 3- FooDB (O)C1OC1OC(CO)C(O)C(O)C1O)C2═O sophoroside CC1OC(OC2C(OC3CCC4(C)C(CCC5(C)C4CCC4C6C7(CC54CO7)OC(CC Hoduloside V FooDB 6(C)O)C═C(C)C)C3(C)C)OC(CO)C(O)C2OC2OC(CO)C(O)C(O)C2O)C(O) C(O)C1O COC1═C(O)C═CC(\C═C\C(═O)OCCCCCCCCCCCCCCCCCCCCCCCCCC 1,26- FooDB OC(═O)\C═C\C2═CC(OC)═C(O)C═C2)═C1 Hexacosanediol diferulate CCCCCCCCCCCC(O)CCCCCCCCCCCCCCCCCO (+)-1,18- FooDB Nonacosanediol CC(OC1OC(CO)C(O)C(O)C1O)\C═C\C1C(C)CC(═O)CC1(C)C 9-Hydroxy-7- FooDB megastigmen-3- one glucoside CCCCCCCCCCCCCCCC(═O)NCC1═CC═CC═C1 Macamide B FooDB NC(═O)CC1═CC═CC2═C1C═CC═C2 2-(1- FooDB Naphthyl)acetamide COC1═C(O)C═C2C3OC(O)C4═C(C═CC5═C4OCO5)C3N(C)CCC2═C1 N-Methyl-14-O- FooDB demethylepiporphyroxine CC1C2C3CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CC(O)C2(C)C(O)C═ Heliantriol C FooDB C1C CC(═C)C1CCC(C)(O)C2CCC(C)(O)C2C1 Guaidiol FooDB OC(═O)COC1═CC2═CC═CC═C2C═C1 (2- FooDB Naphthalenyloxy)acetic acid CCC(SSCC═C)S(═O)\C═C\C 2-Propenyl 1-(1- FooDB propenylsulfinyl)propyl disulfide CC(C)═CCC1═C2CCC3═CC(O)═C(O)C═C3C2═C(O)C═C1O Gancaonin V FooDB OC1OC(COC2OC(COC3OCC(O)C(O)C3O)C(O)C2O)C(O)C1O beta-D- FooDB Xylopyranosyl-(1-> 5)-alpha-L- arabinofuranosyl- (1->5)-L-arabinose CC1OC(OCC2OC(OC3═C(OC4═CC(O)═CC(O)═C4C3═O)C3═CC═C(O)C═ Biorobin FooDB C3)C(O)C(O)C2O)C(O)C(O)C1O CC1(C)C(CCC2(C)C1CCC1(C)C2C(═O)C═C2C3CC(C)(CCC3(C)CCC12C) Licoricesaponin FooDB C(═O)OC1OC(CO)C(O)C(O)C1O)OC1OC(C(O)C(O)C1OC1OC(C(O)C(O) A3 C1O)C(O)═O)C(O)═O CC(C)═CCC(O)C1═CC(═O)C2═C(O)C═CC(O)═C2C1═O C.I. Natural Red FooDB 20 COC1═C(O)C═CC(═C1)C1═[O+]C2═C(C═C1O[C@@H]1O[C@H](COC(C)═O) Peonidin 3-O- FooDB [C@@H](O)[C@H](O)[C@H]1O)C(O)═CC(O)═C2 (acetylglucoside) CC1OC(OC2═C(OC3═C(C(O)═CC(OC4OC(CO)C(O)C(O)C4O)═C3)C2═O) quercetin 3-O- FooDB C2═CC═C(O)C(O)═C2)C(O)C(O)C1O rhamnoside-7-O- glucoside OCC1OC(C(O)C(O)C1O)C1═C(O)C═C2OC(═CC(═O)C2═C1O)C1═CC═C isovitexin FooDB (O)C═C1 CCCCCCCCCC([O−])═O decanoate FooDB CCCCCCCCCCCCCCCCCC(O)CCCCCCCCCCC Nonacosan-13-ol FooDB OCC(O)C1OC2C(OC(═O)C3═C2C(O)═C(O)C(O)═C3C2═C(O)C(O)═C3OC Castacrenin A FooDB (═O)C4═CC(O)═C(O)C5═C4C3═C2C(═O)O5)C1O COC1═CC(CC\C═C\C(═O)CCC2═CC(OC)═C(O)C(OC)═C2)═CC═C1O Isogingerenone B FooDB OCC1OC(OCC2OC(OC3═C(OC4═CC(O)═CC(O)═C4C3═O)C3═CC═C(O)C═C3) Kaempferol 3-(2G- FooDB C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(O)C(O)C1O glucosylgentiobioside) CC\C═C/C1═CC2═C(C═CC═C2)C(═O)O1 (Z)-3-(1-Butenyl)- FooDB 1H-2-benzopyran- 1-one CC\C═C/C[C@@H]1[C@H](CCCCCC(O)═O)CCC1═O OPC-6:1O FooDB [H][C@]12CCC(═C)[C@@]1([H])[C@@]13OC(═O)C(CCO[C@@H]4O[C@ Cichorioside J FooDB H](CO)[C@@H](O)[C@H](O)[C@H]4O)═C1C═C[C@]2(O)CO3 CC(═O)O[C@H]1[C@]2(C)CC[C@@H](C2)C1(C)C (+)-beta-Fenchyl FooDB acetate CC(C)═CCC1═C(O)C═C2OC3═C(C(═O)C2═C1O)C(CCC(C)(C)O)═C(O)C Garcinone C FooDB (O)═C3 COC1═C(O)C═CC(═C1)C1═[O+]C2═C(C═C1O[C@@H]1O[C@H](CO[C@ Peonidin 3- FooDB @H]3OC(C)[C@H](OC(═O)\C═C\C4═CC(O)═C(O)C═C4)[C@@H](O)[C@H] caffeoyl-rutinoside 3O)[C@@H](O)[C@H](O)[C@H]1O)C(O[C@@H]1O[C@H](CO)[C@@H] 5-glucoside (O)[C@H](O)[C@H]1O)═CC(O)═C2 [H]OC([H])([H])C([H])(OC([H])([H])C([H])([H])C([H])([H])C([H])([H])C(\[H])═C 2-Arachidonyl FooDB (\[H])C([H])([H])C(\[H])═C(\[H])C([H])([H])C(\[H])═C(\[H])C([H])([H])C(\[H])═C(\ glycerol ether [H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])O[H] CC\C═C/C1═CC2═C(C═CC═C2)C(═O)O1 (Z)-3-(1-Butenyl)- FooDB 1H-2-benzopyran- 1-one OCC1OC(OC2═C(OC3═C(C(O)═CC(O)═C3)C2═O)C2═CC(O)═C(O)C(O)═ Theaflavonin FooDB C2C2═C(C═C(O)C(O)═C2O)C2OC3═CC(O)═CC(O)═C3CC2OC(═O)C2═C C(O)═C(O)C(O)═C2)C(O)C(O)C1O COC1═CC2═C(C(═O)C═C(O2)C2═CC═C(O)C═C2)C(O)═C1C \4′,5-Dihydroxy-7- FooDB methoxy-6- methylflavone\ COC1═CC(═CC═C1O)C1═C(OC2OC(COC3OC(C)C(O)C(O)C3O)C(O)C(O) Isorhamnetin 3- FooDB C2OC2OCC(O)(CO)C2O)C(═O)C2═C(O1)C═C(O)C═C2O (2G- apiosylrutinoside) COC1═C(C)C(O)═C2C(═O)C═C(C)OC2═C1 Eugenitin FooDB CCCCCCCCCCCCCCCCCCC(O)CCCCCCCCCCCCC Dotriacontan-14-ol FooDB CC(C)═CCC\C(C)═C\C═C\C(\C)═C\C═C\C(\C)═C\C═C/C═C(\C)/C═C/C═C(\ (15Z)-Lycopene FooDB C)/C═C/C═C(\C)CCC═C(C)C OC(═O)C1CSC(═S)C1 2- FooDB Thioxothiazolidine- 4-carboxylic acid COC(═O)NC1═NC2═C(N1)C═CC═C2 Carbendazim FooDB COC1═C(O)C═CC(\C═C\C(═O)NCCC2═CNC3═C2C(═C(O)C═C3)C2═C3C \4,4″-bis(N- FooDB (CCNC(═O)\C═C\C4═CC(OC)═C(O)C═C4)═CNC3═CC═C2O)═C1 feruloyl)serotonin\ CC(═O)C1═C([O−])OC(C)═CC1═O Sodium FooDB dehydroacetate CCC1═C(C)C═C(C)C═C1 \1,3-Dimethyl-4- FooDB ethylbenzene\ OC1CC(O)(CC(C1O)C(═O)OC1═C(C(O)═C(O)C(O)═C1)C1═C(C═C(O)C(O)═ Theogallinin FooDB C1O)C1OC2═CC(O)═CC(O)═C2CC1OC(═O)C1═CC(O)═C(O)C(O)═C1)C (O)═O OC(═O)C1═CC(O)═C(O)C(OC2═C3C(═O)OC4═C5C(═CC(O)═C4O)C(═O) Sanguisobic acid FooDB OC(C(O)═C2O)═C35)═C1 dilactone CCCCCCCCCCCCGCCCCCCC(═O)CCCCCCCCCCCCC Tritriacontan-14- FooDB one COC1═C(O)C═C(\C═C\C(═O)OC[C@H]2O[C@@H](OC3═CC4═C(C═C(O) Peonidin 3- FooDB C═C4O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[O+]═C3C3═ feruloyl- CC(OC)═C(O)C═C3)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H] digiucoside 5- (O)[C@H]3O)[C@@H](O)[C@@H]2O)C═C1 glucoside CC(C)(O)C(O)CC(═O)C(C)(O)C1C(O)CC2(C)C3CC═C4C(CC(═O)C(═O)C4 Cucurbitacin K FooDB (C)C)C3(C)C(═O)CC12C CC(C)═CCC1═CC(═O)C(C)═C(C)C1═O Plastoquinone FooDB OC1═CC(═CC(O)═C1O)C(═O)OC1OC2COC(═O)C3═C(C(O)═C(O)C(OC4═ Rugosin D FooDB C(C═C(O)C(O)═C4O)C(═O)OC4OC5COC(═O)C6═CC(O)═C(O)C(O)═C6C6═ C(C═C(O)C(O)═C6O)C(═O)OC5C(OC(═O)C5═CC(O)═C(O)C(O)═C5)C4O C(═O)C4═CC(O)═C(O)C(O)═C4)═C3)C3═C(C═C(O)C(O)═C3O)C(═O)OC2 C(OC(═O)C2═CC(O)═C(O)C(O)═C2)C1OC(═O)C1═CC(O)═C(O)C(O)═C1 CC1(C)CCC2(C)C(O)CC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)═C Coflodiol FooDB 2C1 OC[C@H]1O[C@@H](OC2═CC3═C(C([C@H](O3)C3═CC═C(O)C═C3)C3═ Foeniculoside XI FooDB CC(O)═CC4═C3[C@H]([C@@H](O4)C3═CC═C(O)C═C3)C3═CC(O)═CC(O [C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)═C3)C(\C═C/C3═C C═C(O)C═C3)═C2)[C@H](O)[C@@H](O)[C@@H]1O CCC(C)NC(═O)\C═C\CCCCCC\C═C\C1═CC2═C(OCO2)C═C1 Piperchabamide D FooDB COC1═CC═C(\C═C/C)C═C1O Isochavibetol FooDB COC1═CC═C(C═C1)C1═COC2═C(C═CC(OC3OC(COC(═O)CC(O)═O)C(O) Formononetin 7- FooDB C(O)C3O)═C2)C1═O (6″- malonylglucoside) COC1═CC(\C═C\C(═O)OC2C(CO)OC(OCC3OC(OC4═CC5═C(C═C(O)C═ Alatanin 1 FooDB C5O)[O+]═C4C4═CC(O)═C(O)C═C4)C(O)C(O)C3O)C(O)C2O)═CC(OC)═C 1O COC1═C(O)C═CC(═C1)C1═[O+]C2═C(C═C1O[C@@H]1O[C@H](COC(═O) Peonidin 3-(6″- FooDB CC(O)═O)[C@@H](O)[C@H](O)[C@H]1O)C(O[C@@H]1O[C@H](CO)[C malonyl- @@H](O)[C@H](O)[C@H]1O)═CC(O)═C2 glucoside) 5- glucoside [H]OC([H])([H])C([H])(N([H])C(═O)C([H])([H])C([H])([H])C([H])([H])C([H])([H]) Palmitoyl serinol FooDB C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C ([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])O[H] C[C@@H]1O[C@@H](O[C@@H]2[C@H](O)[C@H](O)[C@H](C)OC2C2═ 2″-O-alpha-L- FooDB C(O)C3═C(OC(═CC3═O)C3═CC═C(O)C(O)═C3)C═C2O)[C@H](O)[C@H] Rhamnosyl-6-C- (O)[C@H]1O fucosyl-luteolin COC1═CC(═CC═C1O)C1CC(═O)C2═C(O)C═C(O)C═C2O1 Homoeriodictyol FooDB CC\C═C/C[C@@H]1[C@H](CCCC(O)═O)CCC1═O OPC-4:0 FooDB CC1OC(OC2═CC3═C(C(O)═C2)C(═O)C(OC2OC(C)C(O)C(O)C2O)═C(O3) \Quercetin 3,7- FooDB C2═CC═C(O)C(O)═C2)C(O)C(O)C1O dirhamnoside\ COC1═CC═C(C═C1OC)C1═C(OC)C(═O)C2═C(O1)C═C(O)C(OC)═C2OC \7-Hydroxy- FooDB 3,3′,4′,5,6- pentamethoxyflavone\ COC(═O)C1═C(CC(C)C)C(C2═NCCS2)═C(N═C1C(F)F)C(F)(F)F Thiazopyr FooDB [H]OC([H])([H])C([H])([H])N([H])C(═O)C([H])([H])C([H])([H])C(\[H])═C(\[H])C Docosahexaenoyl FooDB ([H])([H])C(\[H])═C(\[H])C([H])([H])C(\[H])═C(\[H])C([H])([H])C(\[H])═C(\[H])C Ethanolamide ([H])([H])C(\[H])═C(\[H])C([H])([H])C(\[H])═C(\[H])C([H])([H])C([H])([H])[H] OC[C@H]1O[C@@H](OC2═CC(O)═C3C(═O)C(O)═C(OC3═C2)C2═CC═C Quercetin 7- FooDB (O)C(O)═C2)[C@H](O)[C@@H](O)[C@@H]1O glucoside CC(C)C(═C)CC[C@@H](C)[C@H]1CC[C@@]2(C)C3CC[C@H]4C(C)[C@ 24-Methylene-31- FooDB @H](O)CC[C@]4(C)C3═CC[C@]12C nor-5alpha-lanost- 9(11)-3beta-ol OC1C(COC(═O)\C═C\C2═CC═C(O)C═C2)OC(OC2═CC3═C(C═C(O)C═C3 Delphinidin 3-(6-p- FooDB O)[O+]═C2C2═CC(O)═C(O)C(O)═C2)C(O)C1O coumaroylglucoside) [H]OC([H])(C(═O)C([H])([H])[H])C1([H])[N([H])C2═C(N═C(N([H])[H])N([H])C2═O) 1-Hydroxy-2- FooDB N([H])C1([H])[H] oxopropyl tetrahydropterin [H][C@]1(NC(═O)[C@@H]2CCCN2C(═O)[C@@H](CC(C)(C)O)OC(═O)CC Hydroxyhomodestruxin B FooDB NC(═O)[C@H](C)N(C)C(═O)[C@H](C(C)CC)N(C)C1═O)[C@@H](C)CC CC1(C)CC2CC1CC2═C beta-Fenchene FooDB CC1═CCC(CC1)C(C)(O)CO \1-p-Menthene- FooDB 8,9-diol\ OCC1OC(OC2═CC(O)═CC3═C2C═C(OC2OC(CO)C(O)C(O)C2OC2OCC Delphinidin 3- FooDB (O)C(O)C2O)C(═[O+]3)C2═CC(O)═C(O)C(O)═C2)C(O)C(O)C1O sambubioside 5- glucoside COC1═C(O)C═CC(═C1)C1═[O+]C2═C(C═C1O[C@@H]1O[C@H](COC(═O) Peonidin 3-(6″- FooDB \C═C\C3═CC(O)═C(O)C═C3)[C@@H](O)[C@H](O)[C@H]1O)C(O)═CC(O)═C2 caffeoyl- glucoside) CCCCNC(═O)N1C(NC(═O)OC)═NC2═C1C═CC═C2 Benomyl FooDB COC1═CC(═CC(OC)═C1O)C1═[O+]C2═C(C═C1OC1O[C@H](COC(C)═O) Malvidin 3-(6″- FooDB [C@H](O)[C@H](O)[C@H]1O)C(O)═CC(O)═C2 acetyl- galactoside) CC(C)[C@@H]1C[C@H](O)[C@@H](C)C═C1 (−)-trans- FooDB Isomenth-5-en-2- ol CC1═C(O)C(O)═CC(═C1)[C@@]12OC3═CC(O)═CC(O)═C3[C@@H]([C@ Proanthocyanidin FooDB H]1O)C1═C3O[C@@H]([C@H](O)CC3═C(O)C═C1O2)C1═CC═C(O)C(O)═ A2 C1 COC1═C(O)C═CC(\C═C\C(═O)NCCC2═CNC3═C2C(═C(O)C═C3)C2═C3C 4-[N-(p- FooDB (CCNC(═O)\C═C\C4═CC═C(O)C═C4)═CNC3═CC═C2O)═C1 Coumaroyl)serotonin- 4″-yl]-N- feruloylserotonin COC1═C2OC(C(CO)C2═CC(CC2COC(═O)C2CC2═CC(OC)═C(O)C(═C2)C Arctignan E FooDB (CO)C(O)C2═CC═C(O)C(OC)═C2)═C1)C1═CC═C(O)C(OC)═C1 CCCCCCCCCCCCCCCCC(O)CCCCCCCCCCCCCCC Dotriacontan-16-ol FooDB [H]OC(═O)C([H])(N([H])[H])C([H])([H])C(═O)N([H])C([H])(C(═O)O[H])C([H]) L-beta-Aspartyl-L- FooDB ([H])[H] alanine OC[C@H]1O[C@@H](OC2═CC3═C(C(O)═C2)C(═O)C(O[C@@H]2O[C@H] \Quercetin 3,7- FooDB (CO)[C@@H](O)[C@H](O)[C@H]2O)═C(O3)C2═CC(O)═C(O)C═C2)[C@H] diglucoside\ (O)[C@@H](O)[C@@H]1O CCCCCCCCC[C@@H](CC(═O)CCC1═CC═C(C)C(OC)═C1)OC(C)═O Acetoxy-[10]- FooDB gingerol COC1═C(OC)C2═CC(CCCCC(O)CCC3═CC═C(O)C2═C3)═C1OC1OC(CO) Myricanol 5- FooDB C(O)C(O)C1O glucoside CC1═CC[C@@H](O)[C@]2(C)CC[C@@H]3[C@H](OC(═O)C3═C)[C@@H] Santamarin FooDB 12 [H][C@@]12C[C@H](O)[C@]3(O)C[C@]1(CC3═C)[C@@H](C(O)═O)[C@] Gibberellin A87 FooDB 1([H])[C@]3(C)[C@@H](O)C═C[C@@]21OC3═O OC1C(O)C(COC(═O)\C═C\C2═CC═C([O−]) Isogomphrenin II FooDB C═C2)OC(OC2═C(O)C═C3CC(C(O)═O)\[N+](═C\C═C4/CC(NC(═C4)C(O)═O) C(O)═O)C3═C2)C1O COC1═CC(O)═C2C(═O)C(O)═C(OC2═C1)C1═CC═C(O)C═C1 Rhamnocitrin FooDB CCCCCCCCCCCCCC(O)CC(═O)CCC1═CC═C(O)C(OC)═C1 [14]-Gingerol FooDB CC1CC2═CC(C)═C(CCO)C(C)═C2C1═O (R)-Pterosin B FooDB OC1OC2COC(═O)C3═CC(O)═C(O)C(O)═C3C3═C(O)C(O)═C(O)C═C3C(═ Tellimagrandin I FooDB O)OC2C(OC(═O)C2═CC(O)═C(O)C(O)═C2)C1OC(═O)C1═CC(O)═C(O)C (O)═C1 COC1═CC═C(C═C1)C1═COC2═C(C═CC(OC3OC(COC(═O)CC(O)═O)C(O) Formononetin 7- FooDB C(O)C3O)═C2)C1═O (6″- malonylglucoside) COC1═C(OC2═C(C(O)═CC(O)═C2)C1═O)C1═CC═CC═C1 3-Methylgalangin FooDB OCC(OC1OCC(O)C(O)C1O)C(O)C(O)C═O 4-O-alpha-D- FooDB Xylopyranosyl-D- xylose CCCCCCCCCCCCCCCCCCCCCCCC(═O)CCCCCCCCC Tritriacontan-10- FooDB one CC12CC(C3═C(C4═C(O3)C═C(C═C4OC(═O)C3═CC═C(O)C═C3O)C3═CC Mulberrofuran M FooDB 4═C(O3)C═C(O)C═C4)C1═O)C1═CC═C(O)C═C1O2 COC1═CC2═C(C═C1OC)C1═C3C(CCN(C)C3═C2C═O)═C(OC)C(OC)═C1OC 7- FooDB Formyldehydrothalicsimidine NC(═N)NCCCCNC(═O)\C═C/C1═CC2═C(OC(C2C(═O)NCCCCNC(N)═N)C Hordatine A FooDB 2═CC═C(OC3OC(CO)C(O)C(O)C3O)C═C2)C(O)═C1 glucoside COC1═CC(═CC═C1O)C(O)C(CO)OC1OC(CO)C(O)C(O)C1O \(1x,2x)- FooDB Guaiacylglycerol 2-glucoside\ COC1═CC(═CC═C1O)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2C1═CC Medioresinol FooDB (OC)═C(O)C(OC)═C1 COC1═C(O)C═CC(═C1)C1═[O+]C2═C(C═C1O[C@@H]1O[C@H](COC(C)═O) \Peonidin acetyl FooDB [C@@H](O)[C@H](O)[C@H]1O)C(O[C@@H]1O[C@H](CO)[C@@H] 3,5-diglucoside\ (O)[C@H](O)[C@H]1O)═CC(O)═C2 CC(C)CNC(═O)\C═C\CCC1═CC2═C(OCO2)C═C1 \4,5- FooDB Dihydropiperlonguminine\ [H]O[C@]([H])(C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])C1([H])C([H]) \(24R)-Cholest-5- FooDB ([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])C([H])═C4C([H])([H])[C@ ene-3-beta,24- @]([H])(O[H])C([H])([H])C([H])([H])[C@]4(C([H])([H])[H])[C@@]3([H])C([H]) diol\ ([H])C([H])([H])[C@]12C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H] [H]C(O)(CO)COC(═O)\C═C\C1═CC═C(O)C═C1 (S)-(+)-1-(p- FooDB Hydroxy-trans- cinnamoyl)- glycerol [H]OC([H])(C(═O)N([H])C([H])([H])C([H])([H])C(═O)N([H])C([H])([H])C([H]) (S)- FooDB ([H])SC(═O)C([H])([H])C([H])(O[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H]) Hydroxyoctadecanoyl- C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C CoA ([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C ([H])([H])OP(═O)(O[H])OP(═O)(O[H])OC([H])([H])C1([H])OC([H])(N2C([H])═ NC3═C2C([H])═C([H])N═C3N([H])[H])C([H])(O[H])C1([H])OP(═O)(O[H])O[H] [H][C@]1(CC(═O)OCCC2═CC(O)═C(O)C═C2)\C(═C/C)[C@H](O[C@@H]2 Demethyloleuropein FooDB O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC═C1C(O)═O OC1OC2COC(═O)C3═C(C(O)═C(O)C(OC4═C(C═C(O)C(O)═C4O)C(═O)O Rugosin E FooDB C4OC5COC(═O)C6═CC(O)═C(O)C(O)═C6C6═C(C═C(O)C(O)═C6O)C(═O) OC5C(OC(═O)C5═CC(O)═C(O)C(O)═C5)C4OC(═O)C4═CC(O)═C(O)C(O)═ C4)═C3)C3═C(C═C(O)C(O)═C3O)C(═O)OC2C(OC(═O)C2═CC(O)═C(O)C (O)═C2)C1OC(═O)C1═CC(O)═C(O)C(O)═C1 OCC1OC(C(O)C(O)C1O)C1═C2OC(═CC(═O)C2═C(O)C═C1O)C1═CC═C Vitexin FooDB (O)C═C1 COC1═C(O)C2═C(C═C1)C1OC3═CC(O)═CC═C3C1CO2 Melilotocarpan B FooDB OC1C(OC2═C(C1C1═C(O)C═C(O)C3═C1OC(C(OC(═O)C1═CC(O)═C(O)C \Epicatechin- FooDB (O)═C1)C3C1═C(O)C═C(O)C3═C1OC(C(C3)OC(═O)C1═CC(O)═C(O)C(O)═ (4beta->8)-ent- C1)C1═CC═C(O)C(O)═C1)C1═CC═C(O)C(O)═C1)C(O)═CC(O)═C2)C1═C epicatechin- C═C(O)C(O)═C1 (4alpha->8)-ent- epicatechin 3′,3″- digallate\ COC1═CC(Cl)═C2NC(═O)C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H] \5-Chloro-2- FooDB (O)[C@H]3O)OC2═C1 hydroxy-7- methoxy-2H-1,4- benzoxazin-3(4H)- one beta-D- glucopyranoside\ COC1═CC(OC)═CC(O)═C1 3,5- HMDB Dimethoxyphenol CC1═C(Cl)C(O)═CC═C1NC1═C(C═CC═C1)C(O)═O N-(2-methyl-3- HMDB chloro-4- hydroxyphenyl)anthranilic acid O(═O)(═O)OC(═O)C1═CNC2═C1C═CC═C2 Indole-3-carboxilic HMDB acid-O-sulphate OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C Maltotridecaose HMDB @H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O [C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C @@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@ @H](O)[C@@H](O[C@H]9[C@H](O)[C@@H](O)[C@@H](O[C@H]%10[C @H](O)[C@@H](O)[C@@H](O[C@H]%11[C@H](O)[C@@H](O)[C@@H] (O[C@H]%12[C@H](O)[C@@H](O)[C@@H](O[C@H]%13[C@H](O)[C@@H] (O)[C@@H](O)O[C@@H]%13CO)O[C@@H]%12CO)O[C@@H]%11CO) O[C@@H]%10CO)O[C@@H]9CO)O[C@@H]8CO)O[C@@H]7CO)O[C@ @H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO)O[C@@H]2CO) [C@H](O)[C@@H](O)[C@@H]1O C[C@@H](O)[C@H](N)C(═O)NC(CCCCN)C(═O)N1CCC[C@H]1C(═O)N[C Tuftsin HMDB @@H](CCCNC(N)═N)C(O)═O NS(═O)(═O)C1═C(Cl)C═C(NCC2═CC═CS2)C(═C1)C1═NNN═N1 Azosemide HMDB COC(═O)\C═C\C(\C)═C\C═C\C(\C)═C\C═C\C═C(/C)\C═C\C═C(/C)\C═C\C beta-Bixin HMDB (O)═O CC(═O)O\C1═C(C)\CCC(CC(O)C(═C)CC1)C(C)(C)O Tanacetol B HMDB OC(═O)C1═CC(OS(O)(═O)═O)═CC═C1 3-hydroxybenzoic HMDB acid-3-O-sulphate OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C Maltohexadecaose HMDB @H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O [C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C @@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@ @H](O)[C@@H](O[C@H]9[C@H](O)[C@@H](O)[C@@H](O[C@H]%10[C @H](O)[C@@H](O)[C@@H](O[C@H]%11[C@H](O)[C@@H](O)[C@@H] (O[C@H]%12[C@H](O)[C@@H](O)[C@@H](O[C@H]%13[C@H](O)[C@@ H](O)[C@@H](O[C@H]%14[C@H](O)[C@@H](O)[C@@H](O[C@H]%15 [C@H](O)[C@@H](O)[C@@H](O[C@H]%16[C@H](O)[C@@H](O)[C@@H] (O)O[C@@H]%16CO)O[C@@H]%15CO)O[C@@H]%14CO)O[C@@H]% 13CO)O[C@@H]%12CO)O[C@@H]%11CO)O[C@@H]%10CO)O[C@@H] 9CO)O[C@@H]8CO)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C @@H]4CO)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H] 1O CC(═O)OCC1OC(OC2═CC3═C(C═C2)C(═O)C(═CO3)C2═CC═C(O)C═C2) 6″-O-Acetyldaidzin HMDB C(O)C(O)C1O COC1═C(Cl)C(C)═C(C(═O)OC2CC3(C)C4CC(C)(C)CC4C(O)C(CO)═C23) Arnamiol HMDB C(O)═C1 CC(CC(O)C1OC2CCC3(CCC(O3)\C═C\C(C)C3CC(C)═CC4(OC(CC(C)(O) Dinophysistoxin 1 HMDB C(O)═O)CCC4O)O3)OC2C(O)C1═C)C1OC2(CCC1C)OCCCC2C CCCCCCCCC═CCCCCCCCC(═O)OCC(COP(O)(O)═O)OC(═O)CCCCCCC 9-Octadecenoic HMDB C═CCCCCCCCC acid 1- [(phosphonoxy)methyl]- 1,2- ethanediyl ester OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C Maltododecaose HMDB @H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O [C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C @@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@ @H](O)[C@@H](O[C@H]9[C@H](O)[C@@H](O)[C@@H](O[C@H]%10[C @H](O)[C@@H](O)[C@@H](O[C@H]%11[C@H](O)[C@@H](O)[C@@H] (O[C@H]%12[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]%12CO)O[C@ @H]%11CO)O[C@@H]%10CO)O[C@@H]9CO)O[C@@H]8CO)O[C@@H] 7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO)O[C @@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O [H][C@@]12CC[C@H](OC(═O)CCCCCC)[C@@]1(C)CC[C@@]1([H])[C@ Testosterone HMDB @]2([H])CCC2═CC(═O)CC[C@]12C enanthate CC1═C(C)C(═O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC═C2CC(CC Coagulin R 3- HMDB (═O)C12C)OC1OC(CO)C(O)C(O)C1O glucoside COC1═C(OC)C═C2C3C[C@@H](O)[C@@H](CC(C)C)CN3CCC2═C1 alpha- HMDB dihydrotetrabenazine O[C@@H]1[C@@H](O)[C@H](OC2═C(O)C═C(CC3CCC(═O)O3)C═C2O) 5-(3′,4′,5′- HMDB O[C@@H]([C@H]1O)C(O)═O Trihydroxyphenyl)- gamma- valerolactone-4′- O-glucuronide OC(CCC(O)═O)CC1═CC═C(OS(O)(═O)═O)C═C1 4-Hydroxy-5-(4′- HMDB hydroxyphenyl)- valeric acid-4′-O- sulphate OS(═O)(═O)ON═O Nitrosylsulfuric HMDB acid NCC(═O)N[C@@H](CCC(N)═O)C(═O)N1CCC[C@H]1C(═O)N[C@@H](CC Rigin HMDB CNC(N)═N)C(O)═O OC(CCCCC(O)═O)CC(O)═O 3-Hydroxysuberic HMDB acid CCC(NC(C)C(═O)N1[C@H]2CCCC[C@H]2C[C@H]1C(═O)O[C@@]1(O[C Perindoprilat HMDB @H](C)[C@@H](O)[C@H](O)[C@H]1O)C(O)═O)C(O)═O glucuronide CC1═C(N)C(C)═C(C(═C1N(═O)═O)C(C)(C)C)N(═O)═O 4-amino-MX HMDB CC(N)COC1═C(C)C═CC═C1CO 2- HMDB hydroxymexiletine CC1CCCC(O)CCCCCC2═CC(O)═CC(O)═C2C(═O)O1 Zeranol HMDB CSCC[C@H](NC(═O)[C@@H](N)CC1═CNC2═CC═CC═C12)C(═O)N[C@ Tetragastrin HMDB @H](CC(O)═O)C(═O)N[C@@H](CC1═CC═CC═C1)C(N)═O CCOC1═C(C═CC(CC(O)═NC(CC(C)C)C2═CC═CC═C2N2CCCC(O)C2)═C hydroxyrepaglinide HMDB 1)C(O)═O OC(CCC(═O)OS(O)(═O)═O)CC1═CC═CC═C1 4-Hydroxy-5- HMDB (phenyl)-valeric acid-O-sulphate OC1OCC2C1COC2C1═CC2═C(OCO2)C═C1 Samin HMDB CC(═O)NC(CSC(═S)NCC═C)C(O)═O N-acetyl-S-(N- HMDB allylthiocarbamoyl)- L-cysteine CCCC1═CC(═O)OC2═C3CC(OC3═C(C(═O)CC(C)C)C(O)═C12)C(C)(C)O Furomammea G HMDB O[C@@H]1[C@@H](COP(O)(═O)OP(O)(═O)OP(O)(O)═O)O[C@H]([C@@ 6-Thioinosine HMDB H]1O)N1C═NC2═C1N═CN═C2S triphosphate CC1OC(CC(O)C1OC1OC(CO)C(O)C(O)C1O)OC1CCC2(C)C(CCC3C2CC Coroloside HMDB C2(C)C(CCC32O)C2═CC(═O)OC2)C1 CCCCC[C@H](O)\C═C\[C@H]1[C@H](O)CC(═O)[C@H]1CCCCCCC(O)═O 8-Isoprostaglandin HMDB E1 CN1C═NC═C1C[C@H](NC(═O)CCCN)C(O)═O Homoanserine HMDB COC(═O)\C═C\C1═CC═C(OC2OC(CO)C(O)C(O)C2O)C═C1 Linocinnamarin HMDB OCC1OC(C(O)C(O)C1O)C1C2═C(C(O)═CC═C2)C(═O)C2═C1C═C(CO)C═ Aloin HMDB C2O CC1═C(C)C(═O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC(O)C4═CC═CC(═O)C Withaperuvin C HMDB 4(C)C3CCC12C OC1═CC═CC2═C1C(═O)C1═C(C═CC═C1O)C2═O Dantron HMDB OC1═CC2═C(C═C1O)C1═C(O2)C(═O)C2═C(OC3═C2C═C(O)C(O)═C3)C1═O Thelephoric acid HMDB NCCCC[C@H](NC(═O)[C@@H]1CCCN1C(═O)[C@@H]1CCCN1)C(═O)N Postin HMDB [C@@H](CCCNC(N)═N)C(O)═O CC1OC(OCC(O)C(O)C(O)C(NC(C)═O)C═O)C(O)C(O)C1O 2-Acetamido-2- HMDB deoxy-6-O-a-L- fucopyranosyl-D- glucose C[N+]1(C)C═CC2═CC(O)═C([O−])C═C12 N,N- HMDB dimethylindoliumolate CCCCNCC(O)C1═CC(Cl)═CC2═C1C1═C(C═C(Cl)C═C1)\C2═C\C1═CC═C desbutyl- HMDB (Cl)C═C1 lumefantrine CC1OC(CC(O)C1O)OC1C(O)CC(OC2CCC3(C)C(CCC4C3CC(O)C3(C)C Digoxigenin HMDB (CCC43O)C3═CC(═O)OC3)C2)OC1C bisdigitoxoside CN1CCC23C4OC5═C(OC6OC(C(O)C(O)C6O)C(O)═O)C═CC(CC1C2CC[C Dihydroisomorphine- HMDB @H]4O)═C35 3-glucuronide N[C@@H](CC1═CC═C(O)C═C1)C(═O)N[C@@H](CCCNC(N)═N)C(O)═O Kyotorphin HMDB CCCCCCCCCCCCCCCCCC(═O)OC(CC([O−])═O)C[N+](C)(C)C Stearoylcarnitine HMDB O[C@H]1[C@H](O)[C@@H](OC2═CC═CC═C2O)O[C@H]([C@@H]1O)C Diphenol HMDB (O)═O glucuronide CCN(CC)C(═S)S(C)═O Methyl-N,N- HMDB diethylthiocarbamate OCCCCC(O)═O 5- HMDB Hydroxypentanoic acid COC1═CC═C(N2CN(C═O)C3═CC═C(OC)C═C3C2)C(CO)═C1 Dictyoquinazol B HMDB OC1═CC═C(C═C1)[C@H]1COC2═C(C1)C═CC(O)═C2 Equol HMDB CNC[C@H]1CCCC[C@]1(O)C1═CC(O)═CC═C1 N,O- HMDB Didesmethyltramadol CN1C(N)═NC2═C1C═CC1═C2N═CC═N1 3-Methyl-3H- HMDB imidazo[4,5- f]quinoxalin-2- amine CC1CCC(\C═C(/C)C═O)C2═C(C)CCC12 Valerenal HMDB OC(CCCC(O)═O)C(O)═O 2-Hydroxyadipic HMDB acid CC1═CC═CC═C1C1OCC(CO)O1 [2-(2- HMDB Methylphenyl)-1,3- dioxolan-4- yl]methanol CCCCCCCCCCCCCCCCCC(═O)SCCNC(═O)CCNC(═O)C(O)C(C)(C)COP Stearoyl-CoA HMDB (O)(═O)OP(O)(═O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)═O)N 1C═NC2═C1N═CN═C2N OC(═O)C1═NCCCC1 D-1-Piperideine-2- HMDB carboxylic acid OC(═O)[C@@H](OC(═O)\C═C\C1═CC(O)═C(O)C═C1)[C@H](OC(═O)\C═ Chicoric acid HMDB C\C1═CC(O)═C(O)C═C1)C(O)═O CC1CS(═O)CC(N1)C(O)═O Cycloalliin HMDB OCC1OC(O[As](O)(O)═O)C(O)C1O Ribose-1-arsenate HMDB O═C1NC2═CC═CC═C2O1 2-Benzoxazolol HMDB C\C(COC1OC(CO)C(O)C(O)C1O)═C/C#N Osmaronin HMDB OC1═C(C═O)C═C(C═C1)C1(NC(═O)NC1═O)C1═CC═CC═C1 Phenytoin HMDB methylcatechol O═C1NC(═O)C2CC═CCC12 3alpha,4,7,7alpha- HMDB Tetrahydro-1H- isoindole-1,3(2H)- dione CCCCCCCCC[C@H](O)CC(═O)SCCNC(═O)CCNC(═O)[C@H](O)C(C)(C) (S)-3- YMDB COP(O)(═O)OP(O)(═O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)═O) hydroxylauroyl- N1C═NC2═C1N═CN═C2N CoA COC1═CC2═C(C(O)═C1O)C(═O)C1═C(C═CC(C)═C1O)C2═O \1,7,8-trihydroxy- PMN 6-methoxy-2- methylanthraquinone\ CC(C)C1═C2C(═O)C(C)CC(═O)C2═C(C═O)C([O−])═C1O hemigossypolone PMN CC(C)C1═C(O)C(O)═C2COC3═CC(C)═CC1═C23 desoxyhemigossypol PMN OCC1OC(OC2═CC3═C(C═C2O)[N+](═CC═C2CC([N+]C(═C2)C([O−])═O) celosianin I PMN C([O−])═O)C(C3)C([O−])═O) C(OC2OC(C(O)C(O)C2OC(═O)C═CC2═CC═C(O)C═C2)C([O−])═O) C(O)C1O [N+]C(CCONC(═[N+])NC(CC([O−])═O)C([O−])═O)C([O−])═O canavaninosuccinate PMN COC1═C(OC)C(OC)═C2C(CCC(N(C)C═O)C3═CC(═O)C(OC)═CC═C23)═C1 N- PMN formyldemecolcine COC1═C(O)C2═C(C(═O)C3═C(C(O)═CC(C)═C3O)C2═O)C(OC)═C1OC \1,4,5-trihydroxy- PMN 6,7,8-trimethoxy- 2- methylanthraquinone\ CCC1═C(C)C2═CC3═C(C═C)C(C)═C4C═C5C(C)C(CCC(═O)OCC═C(C)CC tetrahydrogeranyl PMN CC(C)CCCC(C)CCC═C(C)C)C6═[N+]5[Mg−−] geranyl- 5(N34)N3C(═CC1═[N+]25)C(C)═C1C(═O)[C−](C(═O)OC)C6═C31 chlorophyll a CC(C)═C1CCC2C(CCC3C(C)(CCCC23C)C(O)O)═C1 neoabietadiene- PMN diol COC1═C(OC)C(O)═C2C(═O)C([O−])═C(OC2═C1)C1═CC═C(O)C(O)═C1 eupatolitin PMN OC1═CC2═C(C═C1O)[N+](═CC═C1CC(NC(═C1)C([O−])═O)C([O−])═O) betanidin PMN C(C2)C([O−])═O CCCCCC═CC═COOCCCCCCCC([O−])═O colneleate PMN OCC1OC(CO)(OCC2(OC3OC(CO)C(O)C(O)C3O)OC(CO)C(O)C2O)C(O)C 1-kestotriose PMN 1O CCCCCCC(O)CC═CCCCCCCCC([O−])═O ricinoleate PMN C[N+]1CCC23C4OC5═C(O)C═CC(CC1C2C═CC4═O)═C35 morphinone PMN CCCCCCCCCCCCCCCC(═O)SCCNC(═O)CCNC(═O)C(O)C(C)(C)COP([O−]) palmitoyl-CoA PMN (═O)OP([O−])(═O)OCC1OC(C(O)C1OP([O−])([O−])═O) N1C═NC2═C1N═CN═C2N [N+]CCCC(═O)C([O−])═O 2-keto-ornithine PMN CCC═CCC═CCC═CCCCCCCCC(═O)OCC(COC1OC(CO)C(O)C(O)C1O)O 1-18:3-2-16:3- PMN C(═O)CCCCCC═CCC═CCC═CCC monogalactosyldiacyl glycerol OC1═CC═C2C(═O)C(OC2═C1)C1OC11C═CC(═O)C═C1 phenoxy radical PMN VII CC12CC(O)CC3(OC1═O)C1CCC4(O)CC1(CC4═C)C(C23)C([O−])═O gibberellin A29 PMN CCC1═C(CO)C2═CC3═C(C═C)C(C)═C4C═C5N═C(C(CCC(═O)OCC═C(C) 71- PMN CCCC(C)CCCC(C)CCCC(C)C)C5C)C5═C6N([Mg]N34)C(═CC1═N2)C(C)═ hydroxychlorophylla C6C(═O)[C−]5C(═O)OC CCCCCCCCC1═C(CCCCCCCC([O−])═O)C1 sterculate PMN COC1═CC2═C(C═C1OC)C1C(CO2)OC2═CC(O)═CC═C2C1═O 9- PMN demethylmunduserone COC1═C(OC2═CC([O−])═CC(O)═C2C1═O)C1═CC═C(O)C(O)═C1 3-O- PMN methylquercetin CC(C)═CCNC1═NC═NC2═C1N═CN2C1OC(COP([O−])([O−])═O)C(O)C1O N6-(delta2- PMN isopentenyl)- adenosine 5′- monophosphate COC1═C(O)C═CC(C═CC(O)═CC(═O)C═CC2═CC═C(O)C═C2)═C1 demethoxycurcumin PMN CCC(O)C1CCCC[N+]1 conhydrine PMN COC1═C(OC)C═C(C═C1)C1C2C(COC2═O)C(O)C2═C(OC)C3═C(OCO3)C═ 5′-demethoxy-6- PMN C12 methoxypodophyllotoxin COC1C(O)C(O)C(O)C(O)C1O D-pinitol PMN CCCC1OC(C)═C([O−])C1═O 4-hydroxy-5- PMN methyl-2-propyl- 3(2H)-furanone COC(═O)C1═COC(OC2OC(CO)C(O)C(O)C2O)C(C═C)C1CC═O secologanin PMN COC1═CC23CC[N+](C)C(CC4═CC(OC)═C(OC)C(OC)═C24)CC3═CC1═O O- PMN methylandrocymbine OCC1OC(OC2OC═C3C(CC4N(CC5═CC6═C(C═CC═C6)N═C45)C3═O)C2 deoxypumiloside PMN C═C)C(O)C(O)C1O COC1═CC(═CC═C1O)C(═O)OC1OC(CO)C(O)C(O)C1O 1-O-vanilloyl-beta- PMN D-glucose CSCCCCCC(SC1OC(CO)C(O)C(O)C1O)═NOS([O−])(═O)═O 5- PMN methylthiopentylglucosinolate CC(C)(COP([O−])(═O)OP([O−])(═O)OCC1OC(C(O)C1OP([O−])([O−])═O) 3-hydroxybenzoyl- PMN N1C═NC2═C1N═CN═C2N)C(O)C(═O)NCCC(═O)NCCSC(═O)C1═CC═ CoA CC(O)═C1 OCC1OC(OC2═CC([O−])═ apigeninidin 5-O- PMN CC3═C2C═CC(═[O+]3)C2═CC═C(O)C═C2)C(O)C(O)C1O glucoside OCC1OC(OC2═CC(O)═CC(O)═C2C(═O)C═CC2═CC═C(O)C═C2)C(O)C(O) chalcone 2′-O- PMN C1O glucoside [N+]C(C[Se])C([O−])═O L-selenocysteine PMN O[CH]C═C allyl alcohol PMN [O−]C(═O)CC═CC([O−])═O glutaconate PMN OC1═CC2═C(C═C1)C1OC3═C(C═C4OCOC4═C3)C1(O)CO2 (+)-6a- PMN hydroxymaackiain COC1═CC═C(C2COC3═CC(O)═CC═C3C2)C(O)═C1 (−)-vestitol PMN CC(C)═CCC1═C2OC(CC(═O)C2═C(O)C═C1[O−])C1═C(O)C═C(O)C═C1 leachianone G PMN COC1═C(O)C2═C(C═C1O)C(═O)C1═C(C(O)═CC═C1O)C2═O robustaquinone F PMN COC1═NC2═C(NC(═O)N2C)C(═O)N1C \O(2),1,9- PMN trimethylurate\ COC1═CC2═C(C═C1OC)C1C(CO2)OC2═C(C═CC3═C2CC(O3)C(═C)CO) dalcochinin PMN C1O COC1═CC═C2N═CC═C(C(O)C3CC4CC[N+]3CC4C═C)C2═C1 quinine PMN CCCC═C1OC(C)═C([O−])C1═O (2E)-2-butylidene- PMN 4-hydroxy-5- methyl-3(2H)- furanone [O−]C(═O)CC(═O)CC([O−])═O acetonedicarboxylate PMN [O−]C1═CC(═O)C2═CC═CC═C2C1═O lawsone PMN [N+]C(CN1C(═O)NC═CC1═O)C([O−])═O L-isowillardiine PMN OC1═CC═C(C═C2OC3═CC(O)═CC═C3C2═O)C═C1 hispidol PMN CC1═C(C═C)C(NC1═O)═CC1═C(C)C(CCC([O−])═O)═ biliverdin-IX-alpha PMN C(N1)C═C1N═C(C═C2NC(═O)C(C═C)═C2C)C(C)═C1CCC([O−])═O COC1═C(O)C(CC═C(C)CCC═C(C)CCC═C(C)CCC═C(C)CCC═C(C)CCC═ 2-methoxy-6-(all- PMN C(C)CCC═C(C)CCC═C(C)CCC═C(C)C)═CC═C1 trans- nonaprenyl)phenol COC(═O)C═CC1═CC═CC═C1 methylcinnamate PMN CN1c2cc(NS(═O)(═O)CCc3ccccc3)ccc2OCC(C)(C)C1═O 2-phenyl-N-(3,3,5- Nature trimethyl-4-oxo- 2,3,4,5-tetrahydro- 1,5-benzoxazepin- 7-yl)ethane-1- sulfonamide FC(F)(F)Oc1ccc(NC(═O)NC2CCN(CC2)C(═O)C2CC2)cc1 1-(1- Nature cyclopropanecarbonyl piperidin-4-yl)- 3-[4- (trifluoromethoxy) phenyl]urea CCS(═O)(═O)Nc1ccc(cc1)C(═O)NCC1COc2ccccc2C1 N-[(3,4-dihydro- Nature 2H-1-benzopyran- 3-yl)methyl]-4- ethanesulfonamido benzamide CN(Cc1cccc(NS(N)(═O)═O)c1)C(C)═O N-methyl-N-{[3- Nature (sulfamoylamino)phenyl] methyl}acetamide CC1CCCN(C1)c1nc(C)cc(OCC(═O)Nc2c(C)cccc2C)n1 N-(2,6- Nature dimethylphenyl)-2- {[6-methyl-2-(3- methylpiperidin-1- yl)pyrimidin-4- yl]oxy}acetamide CCOc1ccc(cc1)N(CC)S(═O)(═O)N1CCCC(C1)C(═O)NCc1ccccc1OC 1-[(4- Nature ethoxyphenyl)(ethyl) sulfamoyl]-N- [(2- methoxyphenyl)methyl] piperidine-3- carboxamide [H]C(═O)C1═C[C@@]2(C)C(CC[C@@]3([H])[C@]4([H])CC[C@](C)(O)[C@ Formebolone Nature @]4(C)C[C@@H](O)[C@]23[H])═CC1═O CC1(C)COc2ccc(NS(═O)(═O)Cc3ccc(Cl)cc3)cc2N(CC═C)C1═O 1-(4- Nature chlorophenyl)-N- [3,3-dimethyl-4- oxo-5-(prop-2-en- 1-yl)-2,3,4,5- tetrahydro-1,5- benzoxazepin-7- yl]methanesulfonamide COc1ccccc1C(═O)Nc1ccc2OCC(Cc2c1)C(═O)NCc1ccc(C)cc1 6-(2- Nature methoxybenzamido)- N-[(4- methylphenyl)methyl]- 3,4-dihydro- 2H-1-benzopyran- 3-carboxamide COc1cccc(C2CC(═NN2C(═O)C(C)(C)C)c2cccc(NS(C)(═O)═O)c2)c1O N-{3-[1-(2,2- Nature dimethylpropanoyl)- 5-(2-hydroxy-3- methoxyphenyl)- 4,5-dihydro-1H- pyrazol-3- yl]phenyl}methane sulfonamide Cc1ccc(F)cc1NC(═O)C1COc2ccccc2C1 N-(5-fluoro-2- Nature methylphenyl)-3,4- dihydro-2H-1- benzopyran-3- carboxamide CC(C)CCN1c2ccc(NS(═O)(═O)Cc3cccc(C)c3)cc2OCC(C)(C)C1═O N-[3,3-dimethyl-5- Nature (3-methylbutyl)-4- oxo-2,3,4,5- tetrahydro-1,5- benzoxazepin-8- yl]-1-(3- methylphenyl)methane sulfonamide CC1═CC(═O)C(C)═CC1═O \2,5-Dimethyl-1,4- Nature benzoquinone\ Cc1ccccc1OCCCC(═O)NCC(C)(C)C(N)═O N-(2-carbamoyl- Nature 2,2-dimethylethyl)- 4-(2- methylphenoxy)butanamide CC(NC(═O)C1COc2ccccc2C1)c1ccc(Cl)cc1 N-[1-(4- Nature chlorophenyl)ethyl]- 3,4-dihydro-2H- 1-benzopyran-3- carboxamide Cc1cccc(c1)C(═O)Nc1ccc2OCC(Cc2c1)C(═O)NC1CC1 N-cyclopropyl-6- Nature (3- methylbenzamido)- 3,4-dihydro-2H-1- benzopyran-3- carboxamide FC(F)(F)COc1ccc(OCC(F)(F)F)c(c1)C(═O)NC[C@H]1CCCCN1 N-{[(2R)-piperidin- Nature 2-yl]methyl}-2,5- bis(2,2,2- trifluoroethoxy)benzamide COc1cccc(C(═O)Nc2ccc3N(CC═C)C(═O)C(C)(C)COc3c2)c1OC N-[3,3-dimethyl-4- Nature oxo-5-(prop-2-en- 1-yl)-2,3,4,5- tetrahydro-1,5- benzoxazepin-8- yl]-2,3- dimethoxybenzamide CCOc1ccccc1CCCNC(═O)c1ccc(C)c(NS(C)(═O)═O)c1 N-[3-(2- Nature ethoxyphenyl)propyl]- 3- methanesulfonamido- 4- methylbenzamide CC═C(C)C(═O)OC1CCN2CC═C(COC(═O)C(CO)═CC)C12 Triangularine Nature CCN(CC)Cc1ccccc1NS(N)(═O)═O N-{2- Nature [(diethylamino)methyl] phenyl}aminosulfonamide CN(C)S(═O)(═O)N1CCC(CC1)C(═O)NCCOc1ccccc1C 1- Nature (dimethylsulfamoyl)- N-[2-(2- methylphenoxy)ethyl] piperidine-4- carboxamide CNC(═O)COc1cccc(NS(N)(═O)═O)c1 N-methyl-2-[3- Nature (sulfamoylamino)phenoxy] acetamide CN(C)S(═O)(═O)N1CCC(CC1)C(═O)NC1CC(C)(C)Oc2ccc(C)cc12 1- Nature (dimethylsulfamoyl)- N-(2,2,6- trimethyl-3,4- dihydro-2H-1- benzopyran-4- yl)piperidine-4- carboxamide O═C(NCC1CCCCC1)C1COc2ccc(NC(═O)c3ccccc3)cc2C1 6-benzamido-N- Nature (cyclohexylmethyl)- 3,4-dihydro-2H-1- benzopyran-3- carboxamide C1[C@H]([C@H]([C@@H]([C@H]([C@@H]1O)O)O)O)O Nature C1[C@H]([C@@H]([C@H]([C@H]([C@@H]1O)O)O)O)O Nature C([C@@H]([C@H](CS)O)O)S Nature C(CO)[C@@H]([C@@H](CO)O)O Nature C(CBr)[P@](═O)([O−])O Nature C(C[S@](═O)(═O)[O−])S Nature C(CSCCO)O Nature C1[C@@H]([C@H](O[C@H]1O)CO)O Nature [C@@H]1([C@@H]2[C@@H]([C@@H]3[C@@H]([C@H]1O[C@H](O2)O3) Nature O)O)O C1[C@@H]([C@H](O[C@H]1O[P@](═O)([O−])[O−])CO)O Nature C([C@@H](CS)S)O Nature C([C@H](CS)S)O Nature C([C@H]([C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)O)O Nature C([C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)O Nature C([C@@H]([C@@H]([C@H]([C@H](CO)O)O)O)O)O Nature C([C@H]([C@H]([C@@H]([C@H](CO)O)O)O)O)O Nature C([C@H]([C@H]([C@@H]([C@H]([C@@H](CO)O)O)O)O)O)O Nature [C@H]1([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)O)O)O[P@](═O) Nature ([O−])[O−])O)O C(O)O[C@H]1[C@@H]([C@H]([C@H]([C@H]([C@@H]1O)O)O)O)O Nature C([C@H]([C@H]([C@@H]([C@@H]([C@H](CO)O)O)O)O)O)O Nature C([C@H]([C@@H]([C@H]([C@H](CO)O)O)O)O)O Nature C([C@@H]([C@H]([C@@H]([C@H](CO)O)O)O)O)O Nature C([C@H]([C@@H]([C@H]([C@@H](CO)O)O)O)O)O Nature C([C@H]([C@@](CO)(CO)O)O)O Nature C([C@H](CO)O)O Nature C([C@H]([C@@H]([C@@H]([C@H](CO)O)O)O)O)O Nature C([C@H]([C@H](CO)O)O)O Nature C([C@@H]([C@H](CO)O)O)O Nature C([C@H]([C@@H](CO)O)O)O Nature C(CO)O Nature C([C@@H]1[C@H]([C@H]([C@@H](O1)O[P@](═O)([O−])[O−])O)O)O Nature C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[P@](═O)([O−])[O−]) Nature O)O)O)O C([C@H]([C@@H]([C@H](CO)O)O)O)O Nature C([C@@H]1[C@H]([C@H]([C@@H](O1)O)O)O)O Nature C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)O)O)O)O Nature Nature

TABLE 3 SMILES STRUCTURES CC(C)CC(=O)OCCC(C)CCCC(C)=C CCCCCCCCCCCCC1CCC(=O)O1 NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O COC1=CC2=C(NC=C2CCNC(C)=O)C=C1 C\C(CCC=C)=C/CC[C@](C)(O)C=C CCCC\C=C/CCOC(=O)CC CN(C)C(=N)NCCC[C@H](N)C(O)=O [H]OC1([H])C([H])([H])OC(=O)C([H])([H])C([H])([H])C1([H])O[H] OC[C@@]1(O)CO[C@@H](OC[C@H]2O[C@@H](OC3=CC4=C(C(O)=C3)C(=O)C= C(O4)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H]1O [H]OC([H])(C(=O)N([H])C([H])([H])C([H])([H])C(=O)N([H])C([H])([H])C([H])([H])SC(=O)C([H])(C([H]) ([H])[H])C([H])(O[H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C1([H])C([H])([H])C([H])([H])C2 ([H])C3([H])[C@]([H])(O[H])C([H])([H])[C@]4([H])C([H])([H])[C@]([H])(O[H])C([H])([H])C([H])([H]) C4(C([H])([H])[H])C3([H])C([H])([H])[C@]([H])(O[H])C12C([H])([H])[H])C(C([H])([H])[H])(C([H]) ([H])[H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])=NC 3=C2N=C([H])N=C3N([H])[H])[C@]([H])(O[H])[C@]1([H])OP(=O)(O[H])O[H] [H]OC([H])(C(=O)N([H])C([H])([H])C([H])([H])C(=O)N([H])C([H])([H])C([H])([H])SC(=O)C([H])(C(=O) C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C1([H])C([H])([H])C([H])([H])[C@@]2([H])C3([H])[C@] ([H])(O[H])C([H])([H])[C@]4([H])C([H])([H])[C@]([H])(O[H])C([H])([H])C([H])([H])C4(C([H])([H]) [H])[C@@]3([H])C([H])([H])[C@]([H])(O[H])C12C([H])([H])[H])C([H])([H])[H])C(C([H])([H])[H]) (C([H])([H])[H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@@]1([H])O[C@@]([H]) (N2C([H])=NC3=C2N=C([H])N=C3N([H])[H])[C@]([H])(O[H])[C@]1([H])OP(=O)(O[H])O[H] [H]O[C@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@@]([H])(C1([H])[H])C([H])([H]) [C@@]([H])(O[H])[C@@]1([H])[C@]3([H])C([H])([H])C([H])([H])[C@]([H])([C@]([H])(C([H])([H])[H]) C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]3(C([H])([H])[H])C ([H])([H])C([H])([H])[C@]21[H] [H]O[C@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])C([H])(C1([H])[H])C([H])([H])[C@@] ([H])(O[H])C1([H])C3([H])C([H])([H])C([H])([H])C([H])(C([H])(C([H])([H])[H])C([H])([H])C([H])([H]) C([H])([H])C([H])(C([H])=O)C([H])([H])[H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])C21[H] [H]OC(=O)C([H])([H])N([H])C(=O)C([H])(N([H])[H])C([H])([H])[H] [H]OC([H])(C(=O)N([H])C([H])([H])C([H])([H])C(=O)N([H])C([H])([H])C([H])([H])SC(=O)C(=C([H])C ([H])([H])C([H])([H])C([H])(C([H])([H])[H])C1([H])C([H])([H])C([H])([H])C2([H])C3([H])[C@]([H]) (O[H])C([H])([H])[C@]4([H])C([H])([H])[C@]([H])(O[H])C([H])([H])C([H])([H])[C@]4(C([H])([H])[H])C3 ([H])C([H])([H])C([H])([H])[C@]12C([H])([H])[H])C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C ([H])([H])OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])=NC3=C2N= C([H])N=C3N([H])[H])[C@]([H])(O[H])[C@]1([H])OP(=O)(O[H])O[H] [H]OC([H])(C(=O)N([H])C([H])([H])C([H])([H])C(=O)N([H])C([H])([H])C([H])([H])SC(=O)C([H])(C(=O) C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C1([H])C([H])([H])C([H])([H])C2([H])C3([H])[C@]([H]) 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We claim:
 1. A composition comprising an isolated sweet taste modulator compound selected from the compounds in Table 1, and derivatives thereof, wherein said composition further comprises at least one sweetener.
 2. An ingestible composition comprising a composition of claim 1 and an acceptable carrier for ingestion.
 3. The ingestible composition of claim 1, wherein the sweetener is selected from natural caloric sweeteners, natural high-potency sweeteners, and synthetic sweeteners.
 4. The ingestible composition of claim 2, which has an enhanced sweet taste as compared to an ingestible composition that does not have a compound from Table 1, or a derivative thereof, but is otherwise the same.
 5. The ingestible composition of claim 2, wherein the ingestible composition is a food, beverage, pharmaceutical, nutraceutical, tobacco, or oral hygiene/cosmetic product.
 6. A flavoring concentrate formulation comprising a composition of claim 1 and a carrier. 